97517-66-3|tert-Butyl (5-methylisoxazol-3-yl)carbamate| Ambeed

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1
[ 1072-67-9 ]
[ 24424-99-5 ]
[ 97517-66-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 5-methylisoxazol-3-ylamine; di-<i>tert</i>-butyl dicarbonate With pyridine at 20℃; Stage #2: With methanol; sodium hydroxide; water at 20℃; for 3h;	8.a REFERENCE EXAMPLE 8; (4-Formyl-5-methyl-isoxazol-3-yI)-carbamic acid tert-butyl ester; a) (5-Methyl-isoxazoI-3-yl)-carbamic acid tert-butyl ester; To a solution of 3-amino-5-methylisoxazole (5 g, 51 mmol) in pyridine (80 mL), di-tert-butyl dicarbonate (11.1 g, 51 mmol) was added at room temperature . The reaction was stirred overnight. NaOH aq. in MeOH was added and stirred for 3 h at room temperature. EtOAc and water were added and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using heptane-EtOAc mixtures of increasing polarity as eluent, to afford 6.44 g of the title compound (yield: 63%)
	With sodium hydroxide 1.) pyridine, room temp., 2.) MeOH; Yield given. Multistep reaction;
	With pyridine at 0 - 20℃; for 13h;	1.04; 2.07; 3.08; 4.05; 5.01; 6.05; 7.01; 8.08; 9.07; 10.01; 11.01; 12.01; 13.08; 14.08; 15.08; 16.06; 17.05; 18.04; 19.01; 20.05; 21.08; 22.08; 23.08; 24.06 STEP04: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP07: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP08: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP05: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature for 12 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; 3-[4-(5, 7-diethyl-2-oxo-2H-[l, 6] napthyridin-l-ylmethyl)-phenyl]-thiophene-2-sulphonic acid (4,5-dimethyl-isoxazol-3-yl)-amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP05: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; Example 7; 3-[4-(5, 7-diethyl-2-oxo-2H-[l, 6] naphthyridin -l-yl-methyl)-phenyl]-5-methyl-thiophene- 2-sulphonic acid-(4,5 dimethyl-isoxazol-3-yl)-amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP08: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP07: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; Example 10; 3-[4-(2-metiiyl-qumolin-4-yloxymetyl)-phenyl]-thiophene-2-sulphonic acid (4,5-dimethyl- isoxazol-3-yl)-amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; 3-[4-(5, 7-Diethyl-2-oxo-2H-[l,6]naphthyridin-l-ylmethyl)-2-ethoxymethyl-phenyl]-5- methyl-thiophene-2-sulphonic acid-(4,5-dimethyl-isoxazol-3-yl)-amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; Example 12; 3 - [4-(3 - Acetyl-2,6-dimethyl-pyridine-4-yloxymethyl)-2-ethoxymethyl-phenyl] -5-methyl- ihiophene-2-sulphonic acid(4,5-dimethyl-isoxazol-3-yl)-amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP08: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gni) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP08: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl20 dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium 25 sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP08: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3~ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP06: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP05: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature for 12 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; STEP04: Synthesis of (5~methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.; Example 19; 3-[4-(5,7-Dieyl-2-oxo-2H-[l,6]naphthyridin-l-ylmeyl)-2-methyl-phenyl]-5-methyl- thiophene-2-sulphonic acid(4,5-dimethyl-isoxazol-3yl)-(2-methoxy-ethoxymethyl)amide; STEPOl: Synthesis of (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; 5-methyl-isoxazol-3-ylamine (100 gm, 1.019 mol) was dissolved in pyridine (200 ml, o 2.545 mol) and then cooled this mixture to 0 C. To this reaction mixture di-tert-butyl dicarbonate (245 gm, 1.12 mol) was added in 1 hr. After the completion of the addition, the reaction mixture was stirred at room temperature forl2 hrs. Then the reaction mixture was o concentrated at 60-70 C under vacuum. The residue thus obtained was dissolved in (500 ml) ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid followed by water and brine washings. Finally organic layer was dried over sodium sulphate and evaporated under vacuum to give crude product. The crude product was dissolved in hot toluene (200 ml) and upon standing for 2 hrs at room temperature the solid crystallized out, which was filtered off, washed with cold toluene(50 ml) and suction dried to give (130 gm) of (5-methyl-isoxazol-3-yl)carbamic acid tert-butyl ester.

Reference： [1]Current Patent Assignee: PALAU PHARMA SA - WO2006/13095, 2006, A2 Location in patent: Page/Page column 46
[2]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]
[3]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - WO2007/100295, 2007, A1 Location in patent: Page/Page column 34-35; 45-46; 56-57; 66-67; 74; 84; 92; 103-104

2
[ 124-38-9 ]
[ 97517-66-3 ]
(3-tert-Butoxycarbonylamino-isoxazol-5-yl)-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium diisopropyl amide

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

3
[ 97517-66-3 ]
C₉H₁₂LiN₂O₃^(1-)*Li⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran from -78 deg C up to 25 deg C;

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

4
[ 624-92-0 ]
[ 97517-66-3 ]
(5-methyl-4-methylsulfanyl-isoxazol-3-yl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: Dimethyldisulphide In tetrahydrofuran at -78℃;

Reference： [1]Kanda, Yasuhiko; Takahashi, Tadashi; Araki, Yoshitaka; Konoike, Toshiro; Mihara, Shin-ichi; Fujimoto, Masafumi [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1875 - 1878]

5
[ 59014-89-0 ]
[ 97517-66-3 ]
[4-(3-methoxy-phenylsulfanyl)-5-methyl-isoxazol-3-yl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: bis(3-methoxyphenyl)disulfide In tetrahydrofuran at -78℃;

Reference： [1]Kanda, Yasuhiko; Takahashi, Tadashi; Araki, Yoshitaka; Konoike, Toshiro; Mihara, Shin-ichi; Fujimoto, Masafumi [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1875 - 1878]

6
[ 100-39-0 ]
[ 97517-66-3 ]
[ 174079-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: benzyl bromide In tetrahydrofuran at -78℃;

Reference： [1]Kanda, Yasuhiko; Takahashi, Tadashi; Araki, Yoshitaka; Konoike, Toshiro; Mihara, Shin-ichi; Fujimoto, Masafumi [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1875 - 1878]

7
[ 75-03-6 ]
[ 97517-66-3 ]
[ 174079-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: ethyl iodide In tetrahydrofuran at -78℃;

Reference： [1]Kanda, Yasuhiko; Takahashi, Tadashi; Araki, Yoshitaka; Konoike, Toshiro; Mihara, Shin-ichi; Fujimoto, Masafumi [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1875 - 1878]

8
[ 97517-66-3 ]
[ 74-88-4 ]
[ 174078-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: methyl iodide In tetrahydrofuran at -78℃;
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -78℃; for 1.5h; Stage #2: methyl iodide In hexane at -10℃; for 4h; Stage #3: With water; ammonium chloride In hexane	1.05; 2.08; 3.09; 4.06; 5.02; 6.06; 7.02; 8.09; 9.08; 10.02; 11.02; 12.02; 13.09; 14.09; 15.09; 16.07; 17.06; 18.05; 19.02; 20.06; 21.09; 22.09; 23.08; 24.07 STEP05: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP08: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C. The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP09: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP06: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C. The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP06: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; ,N H-K VVUnder the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 his.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP09: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs. Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP08: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N' -terra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethγl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C. The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP09: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP09: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP09: Synthesis of (4,5-dimethyl-isoxazol-3-vD carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP07: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C. The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP06: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP05: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N.'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C.The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs.Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; STEP02: Synthesis of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.; Under the dry nitrogen atmosphere (5-methyl-isoxazol-3-yl) carbamic acid tert-butyl ester (20 gm, O.lOmol) was dissolved in hexane (150 ml) and N, N, N,'N'-tetra methyl ethylene diamine (35 ml, 0.221mol) was added to it. This reaction mixture was then cooled to - o 78 C. To the reaction mixture n-butyl lithium (106 ml, 0.250 mol, 15% solution in hexane) o was charged in 30 minutes maintaining the temperature of the reaction mixture at -78 C. The reaction mixture was stirred for 1 hr and methyl iodide (12 ml, 0.15mol) was added to o it. After the completion of the addition, the reaction mixture was stirred at -10 C for 4 hrs. Then the reaction mixture was quenched with the saturated solution of ammonium chloride (60 ml). The solid thus obtained was filtered off, washed with cold hexane (50 ml) and suction dried to give 22 gm of (4,5-dimethyl-isoxazol-3-yl) carbamic acid tert-butyl ester.

Reference： [1]Kanda, Yasuhiko; Takahashi, Tadashi; Araki, Yoshitaka; Konoike, Toshiro; Mihara, Shin-ichi; Fujimoto, Masafumi [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1875 - 1878]
[2]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - WO2007/100295, 2007, A1 Location in patent: Page/Page column 35; 46; 57; 67; 74-75; 84; 92-93; 104; 114-115

9
[ 97517-66-3 ]
[ 174078-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C / also with other electrophiles

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

10
[ 97517-66-3 ]
[ 174079-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

11
[ 97517-66-3 ]
[ 174079-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

12
[ 97517-66-3 ]
(4-Allyl-5-methyl-isoxazol-3-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

13
[ 97517-66-3 ]
[ 913535-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

14
[ 97517-66-3 ]
3-tert-Butoxycarbonylamino-5-methyl-isoxazole-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C 3: tetrahydrofuran

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

15
[ 97517-66-3 ]
[ 174079-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

16
[ 97517-66-3 ]
(5-Methyl-4-trimethylsilanyl-isoxazol-3-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

17
[ 97517-66-3 ]
(5-Methyl-4-phenylsulfanyl-isoxazol-3-yl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / from -78 deg C up to 25 deg C 2: tetrahydrofuran / 25 °C

Reference： [1]Konoike, Toshiro; Kanda, Yasuhiko; Araki, Yoshitaka [Tetrahedron Letters, 1996, vol. 37, # 19, p. 3339 - 3342]

18
[ 1112968-97-4 ]
[ 97517-66-3 ]
[ 1112969-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 35℃; for 0.75h; Stage #2: C₁₆H₁₅F₃N₂O₆S In N,N-dimethyl-formamide; mineral oil at 50℃; for 1.5h;	4 Example 4; Compound of Structure Scheme for Compound of Example 4: Intermediate 9. NaH (60% in mineral oil, 7 mg, 0.18 mmol) was added with stirring to tert-butyl 5-methylisoxazol-3-ylcarbamate (34 mg, 0.17 mmol) in DMF (1 mL) at 0° C. The mixture was stirred at this temperature for 15 min, and then at 35° C. for 30 min. The Intermediate 6 (60 mg, 0.14 mmol) in DMF (1.00 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by column chromatography (2% MeOH/DCM) to afford the product that was used for the next step without purification.
	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With sodium hydride In N,N-dimethyl-formamide at 0 - 35℃; for 0.75h; Stage #2: C₁₆H₁₅F₃N₂O₆S In N,N-dimethyl-formamide at 50℃; for 1.5h;	6 NaH (60% in mineral oil, 7 mg, 0.18 mmol) was added with stirring to tert-butyl 5-methylisoxazol-3-ylcarbamate (34 mg, 0.17 mmol) in DMF (1 mL) at 0° C. The mixture was stirred at this temperature for 15 min, and then at 35° C. for 30 min. The Intermediate 22 (60 mg, 0.14 mmol) in DMF (1.00 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by column chromatography (2% MeOH/DCM) to afford the product that was used for the next step without purification.

Reference： [1]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2010/204477, 2010, A1 Location in patent: Page/Page column 18
[2]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2009/48305, 2009, A1 Location in patent: Page/Page column 20

19
[ 3405-77-4 ]
[ 75-65-0 ]
[ 97517-66-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	With diphenylphosphoranyl azide; triethylamine for 18h; Reflux;	31.1 Step 1 To a solution of compound 31a (3.0 g, 22.6 mmol) in tBuOH (50 mL) was added Et3N (6.34 mL, 45.2 mmol) followed by DPPA (5.35 mL, 24.8 mmol). The resulting reaction was heated to reflux for 18 hours, then cooled to room temperature and concentrated in vacuo. The residue obtained was dissolved in dichloromethane, washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated in vacuo to provide a crude residue which was purified using flash column chromatography (EtOAc/Hexanes, 1:9 then 1:6) to provide compound 31b (2.0 g, 45%).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2011/166124, 2011, A1 Location in patent: Page/Page column 47

20
[ 97517-66-3 ]
[ 1215121-86-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 48h; Reflux;	31.2 Step 2 To a solution of compound 31b (1.55 g, 7.83 mmol) in CCl4 (20 mL) was added NBS (5.58 g, 30.3 mmol) and benzoyl peroxide (283 mg, 1.17 mmol). The resulting reaction was heated to reflux for 48 hours, then cooled to room temperature, diluted with dichloromethane, washed with 10% Na2S2O3, brine, dried over Na2SO4 and concentrated in vacuo. The residue obtained was purified using flash column chromatography (EtOAc/Hexanes, 1:9 then 1:6) to provide compound 31c (1.20 g, 56%).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2011/166124, 2011, A1 Location in patent: Page/Page column 47

21
[ 97517-66-3 ]
C₂₉H₃₇F₂N₅O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 48 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2011/166124, 2011, A1

22
[ 97517-66-3 ]
tert-butyl (2-(azetidin-1-ylmethyl)-3,6-difluorobenzyl)(4-(N-(tert-butoxycarbonyl)-N-(5-methylisoxazol-3-yl)sulfamoyl)-3,5-difluorophenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.42 h / -78 - 20 °C 1.2: 18 h / -78 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 20 °C 2.2: 1 h / 20 °C

Reference： [1]Current Patent Assignee: XENON PHARMACEUTICALS INC - US2018/162868, 2018, A1

23
[ 97517-66-3 ]
[ 220239-64-5 ]
tert-butyl (5-methylisoxazol-3-yl)((2,4,6-trifluorophenyl)sulfonyl)-carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: tert-butyl (5-methylisoxazol-3-yl)carbamate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 0.416667h; Stage #2: 2,4,6-trifluorobenzenesulphonyl chloride In tetrahydrofuran at -78 - 20℃; for 18h;	216.1 Step 1. Preparation of tert-butyl (5-methylisoxazol-3-yl)((2,4,6-trifluorophenyl)sulfonyl)-carbamate To a solution of tert-butyl (5-methylisoxazol-3-yl)carbamate (1.98 g, 10.0 mmol) in anhydrous tetrahydrofuran (20 mL) at -78° C. was added lithium bis(trimethylsilyl)amide 1M solution in tetrahydrofuran (11.0 mL, 11.0 mmol). The reaction mixture was stirred at -78° C. for 15 minutes, then warmed up to ambient temperature and stirred for 10 minutes. The reaction mixture was cooled to -78° C. and a solution of 2,4,6-trifluorobenzenesulfonyl chloride (2.30 g, 10.0 mmol) in anhydrous tetrahydrofuran (20 mL) was added to it. The reaction mixture stirred at -78° C. for 2 h and then allowed to warm to ambient temperature. After stirring at ambient temperature for 16 h, the reaction mixture was diluted with saturated ammonium chloride (50 mL) and extracted with ethyl acetate (2×40 mL). The combined organic phases were washed with brine (30 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo and trituration of the residue in methanol (10 mL) provided the title compound as a colorless solid (1.51 g, 38% yield): MS (ES+) m/z 393.1 (M+1).

Reference： [1]Current Patent Assignee: XENON PHARMACEUTICALS INC - US2018/162868, 2018, A1 Location in patent: Paragraph 1473-1474

CAS No. :	97517-66-3	MDL No. :	MFCD11976787
Formula :	C₉H₁₄N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	198.22	Pubchem ID :	-
Synonyms :

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 97517-66-3 ] {[proInfo.proName]}

Quality Control of [ 97517-66-3 ]

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Product Details of [ 97517-66-3 ]

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[ 97517-66-3 ] Synthesis Path-Downstream 1~23

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