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[ CAS No. 150736-72-4 ]

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2D
Chemical Structure| 150736-72-4
Chemical Structure| 150736-72-4
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CAS No. :150736-72-4MDL No. :MFCD04974275
Formula : C9H19NO3 Boiling Point : 292.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :189.25Pubchem ID :11263954
Synonyms :

Computed Properties of [ 150736-72-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 150736-72-4 ]

Signal Word:DangerClass:8,6.1
Precautionary Statements:P280-P301+P310-P305+P351+P338-P310UN#:2923
Hazard Statements:H301-H314Packing Group:
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Application In Synthesis of [ 150736-72-4 ]

  • Downstream synthetic route of [ 150736-72-4 ]

[ 150736-72-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 5856-62-2 ]
  • [ 24424-99-5 ]
  • [ 150736-72-4 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; at 0℃; Example 45; 2-cyclohexyl-(J S)-(morpholine-4-carbonyl)ethvl (IS(at)S-cyclopropyl-[1,2,4]oxadiazole-3- carbonyl)-propyl carbamate; [0072] Step A; Intermediate 2 is synthesized from commercially available (S)-2- amino-butan-1-ol (1): 1 (10.0 g, 112 mmol, 1.0 eq) is dissolved in 500 mL of dry DCM. Boc anhydride (26.93 g, 123.4 mmol, 1.1 eq) is dissolved in 200 mL of dry DCM and added to 1 at 0C via addition funnel over a period of 1 hour. After the reaction mixture is stirred overnight, it is worked up with 25% NH40H. The organic layer is separated and dried over MgS04. Evaporation of the solvent provides pure 2 in quantitative yield.
100% With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 2h;Inert atmosphere; Step A1: (S)-tert-butyl-1-hydroxybutan-2-ylcarbamate Under an atmosphere of argon, (S)-2-aminobutan-1-ol (5.12 g, 56.3 mmol, Eq: 1.00) was combined with water (20 ml) and dioxane (20 ml) to give a colorless solution. At 0 C., NaOH (2.7 g, 67.5 mmol, Eq: 1.2) and di-tert-butyl dicarbonate (14.7 g, 67.5 mmol, Eq: 1.2) were added, and the reaction was stirred for 2 h at RT. The reaction mixture was poured into 50 ml H2O and extracted with EtOAc (2*75 ml). The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a colorless liquid (11.62 g, quant., MS (m/e)=190.3 [M+H+]).
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 2h; Reference Q; Synthesis of 2(S)-amino-1-(5-methoxymethyl-[1.3.4]oxadiazol-2-yl)-butan-1-ol; Step 1; (,S)-(+)-2-amino-l-butanol (50 g, 561 mmol) in a mixture of water and dioxane (200 mL:200 mL) was cooled to 0 C and mixed with NaOH (26.9 g, 673 mmol) and di-ter/-butyl-dicarbonate (146.96 g, 673 mmol). After the addition, the reaction was allowed to warm toroom temperature. The reaction mixture was stirred for 2 h. After removing the dioxane, theresidue was extracted with EtOAc, then washed with brine and dried with anhydrous MgSC>4,filtered and concentrated. Without further purification, the crude 2(»S)-50c-amino-l-butanol (120 g) was used for next step reaction.
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 2h; Reference O Synthesis of 2 (-AMINO-L- (5-METHOXYMETHYL- [L, 3,4] oxadiazol-2-yl) butanol Step 1 (S)- (+)-2-amino-l-butanol (50 g, 561 mmol) in a mixture of water and dioxane (200 mL : 200 mL) was cooled to 0 C and mixed with NAOH (26.9 g, 673 mmol) and di-tert-butyl- dicarbonate (146.96 g, 673 mmol) was added. After the addition, the reaction was allowed to warm to room temperature and the reaction mixture was stirred for 2 h. After removing the dioxane, the residue was extracted with EtOAc, then washed with brine and dried with anhydrous MGS04, filtered and concentrated. Without further purification, the crude 2 (S)-BOC- AMINO-1-BUTANOL (120 g) was used for next step reaction.
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 2h; (S)- (+)-2-Amino-l-butanol (50 g, 561 mmol) in a mixture of water and dioxane (200 mL of water and 200 mL dioxane) was cooled to 0 C and NaOH (26.9 g, 673 mmol) and di-tert- butyldicarbonate (146.96 g, 673 mmol) were added. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 h. After removing the dioxane, the residue was extracted with EtOAc, then washed with brine and dried with anhydrous MgS04, filtered and concentrated. Without further purification, the crude 2 (S)-Boc-amino-l-butanol (120 g) was used in the next step.
With triethylamine; In tetrahydrofuran; at 20℃; for 3h; Example 13Synthesis of: (55',8/?J2/?)-8-amino-12-(dodecanoyloxy)-5-ethyl-7,15-dioxo-3,14-dioxa-10-thia-6- azahexacosan-l-oic acidStep 1: (S)-tert-but l l-hydroxybutan-2-ylcarbamate[000460] To a solution of (5")-2-aminobutan-l-ol (1 eq) in THF (0.26 M) at 0 C was added di- ieri-butyl carbonate (1 eq) and triethylamine (1 eq). The reaction was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vaccuo; and the residue was diluted in ethyl acetate. The organic solution was washed with water (2x), brine, dried over anhydrous MgS04, and concentrated en vaccuo. The material was carried onto the next step without further purification.
11.62 g With sodium hydroxide; In water; at 0 - 20℃; for 2h;Inert atmosphere; Under an atmosphere of argon, (S)-2-aminobutan-l-ol (5.12 g, 56.3 mmol, Eq: 1.00) was combined with water (20 ml) and dioxane (20 ml) to give a colorless solution. At 0C, NaOH (2.7 g, 67.5 mmol, Eq: 1.2) and di-tert-butyl dicarbonate (14.7 g, 67.5 mmol, Eq: 1.2) were added, and the reaction was stirred for 2 h at RT. The reaction mixture was poured into 50 ml H20 and extracted with EtOAc (2 x 75 ml). The organic layers were dried over Na2S04 and concentrated in vacuo. The title compound was obtained as a colorless liquid (11.62 g, quant., MS (m/e) = 190.3 [M+H+]).
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 2h; Step 1 (S)- (+)-2-amino-l-butanol (50 g, 561 mmol) in a mixture of water and dioxane (200 ml of water and 200 ml dioxane) was cooled to 0 C and mixed with NaOH (26.9 g, 673 mmol) and di-tert-butyl-dicarbonate (146.96 g, 673 mmol). After the addition, the reaction was allowed to warm to room temperature and stirred for 2 h. After removing the dioxane, the residue was extracted with EtOAc, then washed with brine and dried with anhydrous MgS04, filtered and concentrated. Without further purification, the crude (5)-2-Boc-amino-1-butanol (120 g) was used for next step reaction.
With triethylamine; In dichloromethane; General procedure: L-amino alcohol (1 equiv), (Boc)2O (1.2 equiv) and trimethylamine(2 equiv) were added to dichloromethane. The mixture wasstirred under ice bath conditions. The reactionwas followed by TLCand diluted with dichloromethane. The organic phase was washedwith citric acid (1 N) and saturated NaHCO3 then dried over Na2SO4and filtered. The filtrate was concentrated and purified by a silicacolumn to afford compounds 10a-g.

  • 3
  • [ 124-63-0 ]
  • [ 150736-72-4 ]
  • (S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In diethyl ether; at 20℃; for 1h;Inert atmosphere; To an ice cold solution of (S)-tert-butyl(1-hydroxybutan-2-yl)carbamate (9.5 g, 50 mmol) and triethylamine (10.5 mL, 75 mmol) in ether (200 mL) was added methanesulfonyl chloride (4.0 mL, 50 mmol). After 1 h, water was added, and the resulting mixture was extracted with DCM, dried (Na2SO4), filtered, and concentrated to give an oil (13.4 g, 100%) which was used directly without further purification.
With triethylamine; In tetrahydrofuran; at 0℃; for 1h; General procedure: To a solution of 28 (10.0 g, 57.1 mmol) in THF (114 mL) wasadded Et3N (11.9 mL, 85.6 mmol) and methanesulfonyl chloride(4.70 mL, 59.9 mmol) at 0 C. The mixture was stirred at 0 C for1 h and then filtered through a pad of KC flock. The filtrate was concentrated under reduced pressure to obtain (2S)-2-[(tertbutoxycarbonyl)amino]propyl methanesulfonate as a colorless oil. To a solution of the methanesulfonate in DMF (100 mL) wasadded 5-fluoro-2-(1H-pyrazol-3-yl)pyridine 29a (8.40 g,51.4 mmol) and Cs2CO3 (37.2 g, 0.110 mol) at room temperature.After the mixture was stirred at 80 C for 3 h, water was added,and the reaction mixture was extracted with EtOAc. The organiclayer was washed with brine, dried over Na2SO4, filtered, and concentratedunder reduced pressure. The resulting solid was washedwith EtOAc to obtain the title compound 30a as a colorless solid(0.50 g, 3% yield over 2 steps).
With triethylamine; In tetrahydrofuran; at 20℃; for 1.5h;Cooling with ice; Triethylamine (640 mg) and methanesulfonyl chloride (470 mg) were added to a tetrahydrofuran solution (10 ml) containing (S)-tert-butyl(1-hydroxybutan-2-yl)carbamate (600 mg) in an ice bath, followed by stirring at room temperature for 1.5 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and (S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate was thus obtained.
  • 4
  • [ 251325-57-2 ]
  • [ 150736-72-4 ]
  • [ 150736-71-3 ]
  • 5
  • [ 98-59-9 ]
  • [ 150736-72-4 ]
  • [ 352704-76-8 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In dichloromethane; General procedure: To a solution of intermediates 10a-g (1 equiv) in dichloromethane, TsCl (1.2 equiv), DMAP (0.2 equiv) and trimethylamine(3 equiv) were added. The solutionwas stirred at 20 C.The reaction was followed by TLC and quenched with water. Theorganic phase was washed with citric acid (1 N) and saturatedNaHCO3 then dried over Na2SO4 and filtered. The filtrate wasconcentrated and purified by a silica column to afford compounds11a-g as a white solid.
  • 7
  • [ 150736-72-4 ]
  • [ 153371-25-6 ]
YieldReaction ConditionsOperation in experiment
100% Step A2: (S)-tert-butyl 1-oxobutan-2-ylcarbamate Under an atmosphere of argon, oxalyl chloride (7.01 g, 4.75 ml, 55.3 mmol, Eq: 1.00) was combined with CH2Cl2 (100 ml) to give a colorless solution. The reaction was cooled to -60 C. Then dimethyl sulfoxide (10.8 g, 9.8 ml, 138 mmol, Eq: 2.5) diluted in CH2Cl2 (20 ml) was added dropwise at -60 C. The reaction was stirred for 10 min at -60 C. Then (S)-tert-butyl-1-hydroxybutan-2-ylcarbamate (11.62 g, 55.3 mmol, Eq: 1.00) dissolved in 20 ml CH2Cl2 was added dropwise at -70 C. The reaction was allowed to warm to -40 C. for 10 min and then cooled to -70 C. again. A solution of triethylamine (15.7 g, 21.6 ml, 155 mmol, Eq: 2.8) in 20 ml CH2Cl2 was added dropwise. The reaction mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was poured into 100 ml satd. sodium dihydrogenphosphate solution and extracted with ethyl acetate (2*150 mL). The organic layer was back-extracted with brine (1*50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a light yellow oil (11.12 g, quant., MS (m/e)=188.2 [M+H+]).
97% Step B; 2 (1.02 g, 5.39 mmol, 1 eq) is dissolved in 60 mL of dry DCM and cooled to 0C. Trichloroisocyanuric acid (1.32 g, 5.65 mmol, 1.05 eq) is added and mixed for 10 minutes resulting in a white slurry. TEMPO is added (8.8 mg, 0.056 mmol, 0.01 eq) to the chilled reaction mixture which immediately turns orange and additional precipitate is formed. The reaction vessel is removed from the cold bath and the mixture is stirred for additional 45 minutes. The reaction mixture is then filtered through a pad of celite, washed with 5% citric acid followed by saturated bicarbonate, dried over MgS04, filtered, and stripped to yield pure 3 (0.979 g, 97 % yield) which was used immediately in step C.
85% With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 0 - 20℃; for 3.5h; Reference Example 102 tert-butyl[(1S)-1-formylpropyl]carbamate A solution of tert-butyl[(1S)-1-(hydroxymethyl)propyl]carbamate (30.0 g) in dimethyl sulfoxide (300 mL) was ice-cooled under a nitrogen atmosphere, and triethylamine (64.4 mL) and a solution of sulfur trioxide·pyridine complex (80.7 g) in dimethyl sulfoxide (300 mL) were successively added. The mixture was stirred at the same temperature for 30 min and then at room temperature for 3 hr, 1 mol/L aqueous citric acid solution (500 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0?30%) to give the title compound as a white powder (yield: 24.3 g, 85%). 1H-NMR(CDCl3)delta:0.97(3H,dd,J=7.6,7.4 Hz), 1.45(9H,s), 1.54-1.77(1H,m), 1.85-2.02(1H,m), 4.14-4.29(1H,m), 5.11(1H,brs), 9.59(1H,s). mp: 39-43 C.
77% With sodium hypochlorite; sodium hydrogencarbonate; sodium bromide;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; water; at 0 - 20℃; for 1.16667h; To a solution of 2 (S)-Boc-aminobutanol in dichloromethane (10 vol) and water (7 vol) were added at 20 C TEMPO (0. 01 equiv. ), sodium bromide (1 equiv.) and sodium hydrogen carbonate (3 equiv. ). The reaction mixture was stirred at 0 C and diluted bleach (1. 3 equiv. , 9 vol) was added over 40 min. The reaction mixture was stirred for 30 min., and then quenched with aq. thiosulfate. After decantation, and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated in vacuo to dryness, giving 77% of 2 (S)- ( tert-butoxycarbonyl) amino-butyraldehyde as a low- melting solid.
77% To a solution of 2(5)-5oc-aminobutanol (50 g; 264 mmol) in dichloromethane (500mL) and water (350 mL) were added at 20 C TEMPO (0.01 eq), sodium bromide (1 eq) andsodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0 C and diluted bleach(1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at 0 Cand then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane),the organic phase was washed with brine, dried and concentrated in vacua to dryness, giving2(S)-( fert-butoxycarbonyl)aminobutyraldehyde as a low-melting solid (38.1 g; yield: 77%).
77% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; sodium bromide; In dichloromethane; water; at 0℃; for 1.16667h;Product distribution / selectivity; Step 2 To a solution of 2 (59-BOC-AMINOBUTANOL (50 g; 264 mmol) in dichloromethane (500 mL) and water (350 mL) were added at 20 C TEMPO (0. 01 EQ), sodium bromide (1 EQ) and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0 C and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at 0 C and then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated in vacuo to dryness, giving 2 (- (TERT-BUTOXYCARBONYL)-AMINO-BUTYRALDEHYDE as a low-melting solid (38.1 g ; yield: 77%).
77% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; sodium bromide; In dichloromethane; water; at 0 - 20℃; for 1.16667h; To a solution of 2 (S)-Boc-aminobutanol (50 g; 264 mmol) in dichloromethane (500 mL) and water (350 mL) were added at 20 C TEMPO (0.01 eq), sodium bromide (1 eq) and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0 C and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at 0 C and then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated in vacuum to dryness, giving 2 ($)-test- butoxycarbonylaminobutyraldehyde as a low-melting solid (38. 1 g; yield: 77%).
77% Reference U Synthesis of [()-2-AMINO-1-BENZOXAZOL-2-YLBUTAN-1-OL] hydrochloride Step 1 To a solution of benzoxazole (28. 6 g, 240 mmol) in toluene (150 mL) was added during ca 20 min. , at about a 2 M solution of isopropyl-magnesium chloride in THF (120 mL, 240 mmol). The red-brown mixture was stored at [CA-4C] and used as needed. Step 2 To a solution of (S)-2-Boc-aminobutanol (50 g; 264 mmol) in dichloromethane (500 [ML)] and water (350 mL) were added at [20 C] TEMPO (0.01 [EQ),] sodium bromide (1 [EQ)] and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at [0 C] and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at [0] C and then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated [IN VACUO] to dryness, giving [(2-2-(TERT-BUTOXYVARBONYL)-AMINOBUTYRALDEHYDE] as a low-melting solid (38. 1 g ; yield: 77%). Step 3 A solution of [()-2- (TERT-BUTOXYCARBONYL)] amino-butyraldehyde (30 g, 160 mmol) in toluene (150 mL) was added over 30 min. [AT-5 C] to a solution of Grignard reagent of benzoxazole (prepared as described in Step 1 above). The reaction mixture was stirred for 0.5 h at [0 C,] then 2.5 h at RT. Quenching with 5% aq. acetic acid, washings with 5% aq. sodium carbonate, then brine and concentration to dryness gave crude (S)-2- (tert- butoxycarbonyl)-amino-l-benzoxazol-2-yl-butan-l-ol. The residue was diluted with toluene, and silica gel was added. The slurry was filtered. Elution by toluene removed the non-polar impurities. Then an 8/2 mixture of toluene and ethyl acetate desorbed the [(S)-2- (TERT-] butoxycarbonyl) [AMINO-1-BENZOXAZOL-2-YLBUTAN-1-OL.] Step 4 To a solution of [(S)-2- (TERT-BUTOXYCARBONYL) AMINO-L-BENZOXAZOL-2-YL-PROPAN-L-OL] (26.3 g, 86 mmol) in isopropanol (118 mL) at [20-25 C] was added trimethylchlorosilane (1.4 eq). The solution was stirred for 5 h at [50C.] Concentration of the reaction mixture to 52 mL followed by addition of isopropyl ether [(210 ML),] filtration and drying under vacuum afforded [(S)-2-AMINO-1-BENZOXAZOL-2-YLBUTAN-1-OL] hydrochloride salt as a grey solid (16.4 g; yield = 79 %; mixture of diastereomers).
A solution of oxalyl chloride (40.39 g, 265 ramol) in MeCk (700 mL) was stirred andcooled to -60 C. Dimethylsulfoxide (51.7 g, 663 mmol) in MeCl2 (100 mL) was addeddropwise. After 10 min., a solution of 2(
Step 2 A solution of oxalyl chloride (40.39 g, 265 mmol) in CH2C12 (700 mL) was stirred and COOLED TO-60 C. Dimethylsulfoxide (51.7 g, 663 mmol) in CH2C12 (100 mL) was added dropwise. After 10 min, a solution of (6 )-2-8OC-AMINO-L-BUTANOL (50 g, 265 mmol) in CH2C12 (100 mL) was added dropwise AT-70 C. The reaction mixture was allowed to warm to-40 C for 10 min and then cooled to-70 C again. A solution of triethylamine (74.9 g, 742 mmol) in CH2CI2 (100 mL) was added. The reaction mixture was allowed to warm to room temperature over 2 h. Saturated sodium dihydrogen phosphate (100 mL) was added, and then the organic layer was washed with brine and dried over MGS04. The solvent was removed to yield 45g of 2 (S)-BOC-AMINO-BUTYRALDEHYDE.
A solution of oxalyl chloride (40. 39 g, 265 mmol) in CH2Cl2 (700 mL) was stirred and cooled to-60 C. Dimethylsulfoxide (51.7 g, 663 mmol) in CH2C12 (100 mL) was added dropwise. After 10 min, a solution of 2 (S)-Boc-amino-l-butanol (50 g, 265 mmol) in CH2CI2 (100 mL) was added dropwise at-70 C. The reaction mixture was allowed to warm to-40 C for 10 min and then cooled to-70 C again. A solution of triethylamine (74.9 g, 742 mmol) in CH2C12 (100 mL) was added and the reaction mixture was allowed to warm to room temperature over 2 h. Saturated sodium dihydrogen phosphate (100 mL) was added and then the organic layer was washed with brine and dried over MgS04. The solvent was removed to yield 45 g of 2 (@-Boc-aminobutyraldehyde (1-formylpropyl) carbamic acid tert-butyl ester.
Reference P Synthesis of [()-2-AMINO-1- (5-METHOXYMETHYL- [1,] 3,4] [OXADIAZOL-2-YL)-BUTAN-1-OL] Step 1 [(S)- (+)-2-AMINO-L-BUTANOL] (50 g, 561 mmol) in a mixture of water and dioxane (200 mL of water and: 200 mL) dioxane was cooled to [0 C] and mixed with [NAOH] (26.9 g, 673 mmol) and di-tert-butyl-dicarbonate (146.96 g, 673 mmol). After the addition, the reaction was allowed to warm to room temperature. The reaction mixture was stirred for 2 h. After removing the dioxane, the residue was extracted with EtOAc, then washed with brine and dried with anhydrous [MGS04,] filtered and concentrated. Without further purification, the crude [(S)-2-BOC-AMINO-L-BUTANOL] (120 g) was used for next step reaction. Step 2 A solution of oxalyl chloride (40.39 g, 265 mmol) in [MECLZ] (700 mL) was stirred and cooled to-60 [C.] Dimethylsulfoxide (51.7 g, 663 mmol) in [MECL2] (100 [ML)] was added dropwise. After 10 min. , a solution of [(S)-2-BOC-AMINO-L-BUTANOL] (50 g, 265 mmol) in [MECL2] (100 mL) was added dropwise [AT-70 C.] The reaction mixture was allowed to warm to-40 C for 10 min. and then cooled to-70 C again. A solution of triethylamine (74.9 g, 742 mmol) in MeCl2 (100 mL) was added. The reaction mixture was allowed to warm to room temperature over 2 h. Saturated sodium dihydrogen phosphate (100 [ML)] was added, and then the organic layer was washed with brine and dried over [MGS04. THE] solvent was removed to yield 45g of [(S)-2-BOC-AMINO-BUTYRALDEHYDE (L-FORMYL-PROPYL)-CARBAMIC] acid [TERT-BUTYL] ester. Step 3 A mixture of methyl methoxyacetate (52 g, 500 mmol), hydrazine hydrate (30 mL) was heated to reflux for 8 h. Excess hydrazine and water were removed under vacuum. The residue was extracted with n-butanol, dried with [NA2SO4.] Excess n-butanol was removed to yield 45g of hydrazide. Step 4 A mixture of above hydrazide (45 g), [TRIETHYLORTHOFORMATE] (146 mL) and p- toluenesulfonic acid (61mg) was heated at [140 C] for 8 h. Excess [TRIETHYLORTHOFORMATE] was removed under vacuum. The product was purified by silica gel column chromatography to yield 4.6g of 2-methoxymethyl-1, 3,4-oxadiazole. Step 5 To a stirred solution of 2-methoxymethyl-1, 3,4-oxadiazole (4.6 g, 40 mmol) in THF (100 mL) was added n-BuLi (1.6 M solution in 25.2 mL of hexane) dropwise under N2 at-78 [C.] After 1 h, MgBr. Et2O (10.4 g, 40.3 mmol) was added and the reaction mixture was allowed to warm to-45 [C] for 1 h before being treated with (S)-2-Boc-amino- propanylaldehyde butyraldehyde (5.28 g, 28.25 mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated [NH4C1,] and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04 and concentrated. The residue was purified by silica gel column chromatography to yield [(S)-2-BOC-AMINO-1- (5-] methoxymethyl-[1, 3, [4]-OXADIAZOLE-2-YL)-1-PROPANOL] butanol (500 mg). Step 6 [2-BOC-AMINO-1- (5-METHOXYMETHYL- [1,] 3, [4]-OXADIAZOLE-2-YL)-1-PROPANOL] butanol (500 mg, 1.66 mmol), and MeCl2 (5 mL) were mixed and TFA (0.5 mL) was added at room temperature. After stirring for 1 h, the solvent and excess TFA were removed under vacuum to produce [(S)-2-AMINO-L- (5-METHOXYMETHYL- [1,] 3,4] oxadiazol-2-yl)-butan-1-ol. TFA salt (340 mg).
11.12 g With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - 20℃; for 2h;Inert atmosphere; Under an atmosphere of argon, oxalyl chloride (7.01 g, 4.75 ml, 55.3 mmol, Eq: 1.00) was combined with CH2CI2 (100 ml) to give a colorless solution. The reaction was cooled to - 60C. Then dimethyl sulfoxide (10.8 g, 9.8 ml, 138 mmol, Eq: 2.5) diluted in CH2C12 (20ml) was added dropwise at - 60C. The reaction was stirred for 10 min at -60C. Then (S)-tert-butyl -l-hydroxybutan-2-ylcarbamate (11.62 g, 55.3 mmol, Eq: 1.00) dissolved in 20ml CH2C12 was added dropwise at -70C. The reaction was allowed to warm to -40C for 10 min and then cooled to -70C again. A solution of triethylamine (15.7 g, 21.6 ml, 155 mmol, Eq: 2.8) in 20 ml CH2C12 was added dropwise. The reaction mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was poured into 100 ml satd. sodium dihydrogenphosphate solution and extracted with ethyl acetate (2 x 150 mL).The organic layer was back-extracted with brine (1 x 50 mL). The organic layers were dried over Na2S04 and concentrated in vacuo. The title compound was obtained as a light yellow oil (11.12 g, quant., MS (m/e) = 188.2 [M+H+]).
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - 20℃; for 2h; A solution of oxalyl chloride (40.39 g, 265 mmol) in CH2Cl2 (700 ml) was stirred and cooled to-60 C. Dimethylsulfoxide (51.7 g, 663 mmol) in CH2Cl2 (100 ml) was added dropwise. After 10 min, a solution of (S)-2-Boc-amino-1-butanol (50 g, 265 mmol) in CH2C12 (100 ml) was added dropwise at-70 C. The reaction mixture was allowed to warm to-40 C for 10 min and then cooled to-70 C again. A solution of triethylamine (74.9 g, 742 mmol) in CH2C12 (100 ml) was added and the reaction mixture was allowed to warm to room temperature over 2 h. Saturated sodium dihydrogen phosphate (100 ml) was added, and then the organic layer was washed with brine and dried over MgS04. The solvent was removed to yield (S)-2-Boc-amino-butyraldehyde (1-formylpropyl) carbamic acid ter-butyl ester (45 g).

  • 8
  • C13H23NO6 [ No CAS ]
  • [ 150736-72-4 ]
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