170853-04-0|tert-Butyl 3-formylbenzylcarbamate| Ambeed

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Quality Control of [ 170853-04-0 ] Purity: 98% SDS Specification

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Product Details of [ 170853-04-0 ]

CAS No. :	170853-04-0
Formula :	C₁₃H₁₇NO₃
M.W :	235.28
SMILES Code :	CC(C)(C)OC(=O)NCC1=CC(C=O)=CC=C1
MDL No. :	MFCD06659091
InChI Key :	JORXNWZTJLYRQA-UHFFFAOYSA-N
Pubchem ID :	2794834

Safety of [ 170853-04-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 170853-04-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 170853-04-0 ]

[ 170853-04-0 ] Synthesis Path-Downstream 1~33

1
[ 875582-81-3 ]
[ 170853-04-0 ]

References: [1]Synthesis,2005,p. 3297 - 3300.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4356 - 4373.

2
[ 170853-04-0 ]
[ 141399-96-4 ]
2-[1'-{3''(tert-butoxycarbonylamino-methyl)-phenyl}-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid [ No CAS ]

References: [1]Synthesis,2005,p. 3297 - 3300.

3
[ 875582-75-5 ]
[ 170853-04-0 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

4
[ 24964-64-5 ]
[ 170853-04-0 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

5
[ 153329-04-5 ]
[ 170853-04-0 ]

References: [1]Synthesis,2005,p. 3297 - 3300.

6
[ 4394-85-8 ]
[ 171663-13-1 ]
[ 170853-04-0 ]

Yield	Reaction Conditions	Operation in experiment
		8.58g of t-Butyl N-(3-bromobenzyl)carbamate was dissolved in 100 ml of tetrahydrofuran, and the mixture was cooled to -78C under nitrogen atmosphere. 41 ml of butyl lithium (1.56 M solution in hexane) was added. After stirring was continued for 30 minutes, 6.91 g of N-formylmorpholine was added. After stirring was continued at -78C for 30 minutes, 1N-hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off, and the residue was purified by silica gel column chromatography, to give 4.762 g of the title compound in the 3:1 ? 3:2 hexane-ethyl acetate fraction.1H-NMR (CDCl3) delta : 1.44 (s, 9H) 4.40 (d, J=6.0Hz, 2H) 4.95 (br, 1H) 7.50 (m, 1H) 7.56-7.59 (m, 1H) 7.78-7.80 (m, 1H) 7.80 (s, 1H) 10.01 (s, 1H)

References: [1]Patent: EP1380562,2004,A1 .Location in patent: Page 108.

7
[ 170853-04-0 ]
[ 334016-00-1 ]
[ 478929-86-1 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 15.3 g of (4S)-4-benzyl-3-(2-isopropoxyacetyl)-1,3-oxazolon-2-one in toluene (250 ml) was cooled to -75C, and 9.0 ml of triethylamine was added thereto. 55 ml of dibutylboron triflate (1M solution in dichloromethane) was added dropwise at such a rate that the inside temperature did not exceed -70C. After the dropwise addition, the mixture was stirred for 50 minutes and then the inside temperature was raised to 0C. The mixture was stirred for another 50 minuets, and again cooled to -75C. To this reaction solution was added a solution containing 9.6 g of <strong>[170853-04-0]t-butyl N-(3-formylbenzyl)carbamate</strong> in dichloromethane (40ml) by means of cannula and the mixture was stirred at -75C for 30 minutes. Then the temperature was raised to 0C over about 1 hour by 10C per 10 minutes. The temperature was gradually raised to room temperature and stirring was continued overnight at room temperature. The reaction solution was poured into a mixed solution of 200 ml of methanol, 200 ml of pH 7 buffer (disodium hydrogen phosphate-citric acid) and 60 ml of hydrogen peroxide (30% aqueous solution), and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 19.2 g of the title compound as a colorless oil in the 1:1 hexane-ethyl acetate fraction.1H NMR (CDCl3) δ : 1.12 (d, J=6.0Hz, 3H) 1.19 (d, J=6.0Hz, 3H) 1.44 (s, 9H) 2.75 (dd, J=10.0, 13.6Hz, 1H) 3.25 (dd, J=2.4, 13.6Hz, 1H) 3.65 (Sept, J=6.0Hz, 1H) 3. 72 (t, J=8.0Hz, 1H) 4.02 (d, J=8.4Hz, 1H) 4.29 (d, J=6.0Hz, 1H) 4.37-4.43 (m, 1H) 4.85 (t, J=4. 8Hz, 1H) 4.91 (m, 1H) 5.43 (d, J=5.6Hz, 1H) 7.12-7.73 (m, 8H) 7.63 (s, 1H)

References: [1]Patent: EP1380562,2004,A1 .Location in patent: Page 177.

8
[ 24424-99-5 ]
[ 39959-54-1 ]
[ 33513-42-7 ]
[ 170853-04-0 ]

Yield	Reaction Conditions	Operation in experiment
		[0262] To a solution of 2.0 g of 3-bromobenzylamine hydrochloride in 20 ml of dioxane-water (1:1) was added 1.5 g of NaHCO3 and a solution of 2.2 g of di-t-butyl dicarbonate in 10 ml of dioxane in order at room temperature, and the mixture was stirred at room temperature for 1 day. Water was added to the reaction mixture and the reaction mixture was extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 3.0 g of a bromo-derivative. The bromo-derivative (3.0 g) was dissolved in 30 ml of THF, to which was added 14 ml of 1.5M butyllithium/hexane solution at -78 C., and the mixture was stirred at the same temperature for 30 minutes. To the resulting solution was added a solution of 1.7 ml of DMF in 10 ml of THF at -78 C., and the mixture was warmed up to -15 C. over 1.5 hours. An aqueous ammonium chloride solution was added to the reaction mixture and extracted with EtOAc. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 0.89 g of t-butyl 3-formylbenzylcarbamate.

References: [1]Patent: US2003/232860,2003,A1 .Location in patent: Page 13.

9
[ 170853-04-0 ]
triethyl phosphonoacetic acid [ No CAS ]
ethyl 3-[(tert-butoxycarbonyl)amino]methyl}cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane; water;	Reference Example 16 374 mg of 60% sodium hydride was suspended in 20.0 mL of dimethoxyethane, and 1.91 g of ethyl diethylphosphonoacetate was added dropwise thereto at -5C, followed by stirring at room temperature for 10 minutes. To the reaction liquid was added dropwise a solution of <strong>[170853-04-0]tert-butyl (3-formylbenzyl)carbamate</strong> in dimethoxyethane (5.00 mL), followed by stirring at 60C for 4 hours. The reaction liquid was cooled to room temperature, followed by addition of water and extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain ethyl 3-[(tert-butoxycarbonyl)amino]methyl}cinnamate.

References: [1]Patent: EP2050446,2009,A1 .

10
[ 170853-04-0 ]
[ 78925-40-3 ]
2-[1'-{3''(tert-butoxycarbonylamino-methyl)-phenyl}-meth-(Z)-ylidene]-3-oxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4356 - 4373.

11
[ 170853-04-0 ]
[ 942947-96-8 ]
[ 942948-10-9 ]

Yield	Reaction Conditions	Operation in experiment
27%	With sodium dithionite; In ethanol; water; at 80℃; for 21h;	To 2-[4-(2-Amino-5-bromo-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (0.1 g, 0.22 mmol) in ethanol (5 ml) was added tert-butyl N-(3 formylbenzyl)carbamate (69 mg, 0.29 mmol) and 1M aq. Na2S2O4 (900 μL, 0.9 mmol). The reaction mixture was stirred at 80 C. for 16 h. tert-Butyl N-(3 formylbenzyl)carbamate (20 mg, 0.08 mmol) and 1M aq. Na2S2O4 (200 μL, 0.2 mmol) were added and the reaction mixture was stirred for another 5 h. The reaction mixture was concentrated in vacuo. The crude product was purified by chromatography on silica gel (100% dichloromethane to dichloromethane/ethyl acetate 1:1+1% methanol to 2% methanol in ethyl acetate). The isolated product was further triturated in ether, filtered, and dried in vacuo to give the title compound as a pale yellow solid (0.038 g, 27%); 1H-NMR (500 MHz, DMSO-d6) 1.39 (s, 9H, CH3 Boc), 2.78 (broad s, 4H, piperazine N(CH2)2), 3.40 (s, 2H, CH2CO), 3.70 (broad s, 4H, piperazine N(CH2)2), 4.22 (d, J=6.23 Hz, 2H, CH2NHBOC), 7.24 (d, 1H, J=3.60 Hz, thiazole 4-H or 5-H), 7.37 (d, J=7.21 Hz, 1H) and 8.02 (d, J=7.21 Hz, 1H) (4-ArH, and 6-ArH), 7.47 (m, 1H, 5-ArH), 7.49 (d, J=4.12 Hz, 1H, thiazole 4-H or 5-H), 8.11 (s, 1H, imidazo[4,5-b]pyridine 5-H), 11.89 (s, 1H, CONH), 13.54 (s, 1H, imidazo[4,5-b]pyridine NH);LC-MS (ESI, m/z) Rt=6.92 min-627, 629 [(M+H+), Br isotopic pattern, 100%];ESI-HRMS Found: 627.1513, calculated for C27H32BrN8O3S (M+H)+: 627.1501.

References: [1]Patent: US2009/247507,2009,A1 .Location in patent: Page/Page column 13.

12
[ 180863-55-2 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

13
[ 6515-58-8 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

14
[ 99-04-7 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

15
[ 1129-28-8 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

16
[ 117445-22-4 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 946 - 979.

17
[ 226070-69-5 ]
[ 170853-04-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 25℃; for 6h;	To a suspension of PCC (360 mg, 1.6 mmol) and sodium acetate (26 mg, 0.32 mmol) in dichloremethane (5.0 mL) was added (3-Hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.84 mmol) in dichloromethane (5.0 mL) and the reaction mixture was stirred at 25 C over a period of 6 h. The resulting mixture was diluted with ethyl acetate (50 mL), filtered through celite pad, the filtrate was washed with water, brine and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give (3- Formyl-benzyl)-carbamic acid tert-butyl ester as brownish oil (180 mg, 94 %).
94%	With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 25℃; for 6h;	To a suspension of PCC (360 mg, 1.6 mmol) and sodium acetate (26 mg, 0.32 mmol) in dichloremethane (5.0 mL) was added (3-Hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.84 mmol) in dichloromethane (5.0 mL) and the reaction mixture was stirred at 25 C. over a period of 6 h. The resulting mixture was diluted with ethyl acetate (50 mL), filtered through celite pad, the filtrate was washed with water, brine and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give (3-Formyl-benzyl)-carbamic acid tert-butyl ester as brownish oil (180 mg, 94%).

References: [1]Patent: WO2011/21209,2011,A1 .Location in patent: Page/Page column 69; 72; 73.
[2]Patent: US2012/101099,2012,A1 .Location in patent: Page/Page column 28; 30.
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 946 - 979.

18
3-aminomethyl-benzoic acid methyl ester hydrochloride [ No CAS ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

19
[ 781632-38-0 ]
[ 170853-04-0 ]

References: [1]Patent: WO2011/21209,2011,A1 .
[2]Patent: US2012/101099,2012,A1 .

20
[ 170853-04-0 ]
N-(piperidin-3-yl)-1H-indazol-5-amine dihydrochioride [ No CAS ]
[ 1035095-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; sodium cyanoborohydride; In methanol; for 18h;	teri-Butyl (3-((3-(lH-indazol-5-ylamino)piperidin-l-yl)methyl)phenyl)methyl carbamateAn equimolar solution of (R)-N-(piperidin-3-yl)-lH-indazol-5-amine dihydrochloride and tert-butyl 3-formylbenzylcarbamate in MeOH containing a twofold molar excess of sodium acetate was treated with a 1.5 molar excess of sodium cyanoborohydride for 18 hours. The reaction was monitored by HPLC for complete conversion of the starting materials to the product and when complete, was quenched with aqueous sodium bicarbonate. The solution was extracted with ethyl acetate, washed with dilute HC1 and brine then dried over MgS04. Evaporation afforded a residue which was chromatographed on silica gel to yield the title compound. 1H NMR (CDC13) 5 9.84(br s,lH), 7.86(s,lH), 7.15-7.3 l(m,5H), 6.80- 6.85(m,2H), 4.8(s,lH), 4.28-4.32(d,2H), 3.95-4.05(s,lH), 3.40-3.62(m,2H), 2.60-2.74(s,lH), 2.14-2.45(m,2H), 1.50-1.80(m,6H), 1.47(s,9H)

References: [1]Patent: WO2012/15760,2012,A1 .Location in patent: Page/Page column 38.

21
[ 170853-04-0 ]
[ 5927-18-4 ]
[ 171662-97-8 ]