39796-52-6|2-Amino-N-benzylacetamide| Ambeed

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Quality Control of [ 39796-52-6 ] Purity: 98% SDS Specification

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Product Details of [ 39796-52-6 ]

CAS No. :	39796-52-6
Formula :	C₉H₁₂N₂O
M.W :	164.20
SMILES Code :	O=C(NCC1=CC=CC=C1)CN
MDL No. :	MFCD09724204
InChI Key :	MYZCBJRJVXAQIV-UHFFFAOYSA-N
Pubchem ID :	11126610

Safety of [ 39796-52-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 39796-52-6 ]

* 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 [ 39796-52-6 ]

[ 39796-52-6 ] Synthesis Path-Downstream 1~35

1
[ 4905-17-3 ]
[ 39796-52-6 ]

References: [1]Acta Chimica Academiae Scientiarum Hungaricae,1959,vol. 21,p. 417,424.
[2]Canadian Journal of Chemistry,1989,vol. 67,p. 2128 - 2135.

2
[ 5680-79-5 ]
[ 100-46-9 ]
[ 39796-52-6 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 567 - 574.
[2]Fermentforschung,1933,vol. 13,p. 97,105,106.

3
[ 2642-32-2 ]
[ 39796-52-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 3h;	General procedure: This procedure is illustrated for compound 11a. To a solution of compound 10a (170 mg, 0.77 mmol) in methanol (10 mL), 10% Pd/C was added. The reaction was hydrogenated at room temperature and atmospheric pressure for 3 h. Then the catalyst was filtered off through Celite, and the clear solution, taken to dryness, afforded the title compound as an oil. The reaction was monitored by TLC and, for stability problems, the amine was directly used in the subsequent reaction. Yield 97%.

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1285 - 1297.
[2]Justus Liebigs Annalen der Chemie,1962,vol. 655,p. 211 - 218.

4
[ 17038-67-4 ]
[ 39796-52-6 ]

References: [1]Journal of the Chemical Society C: Organic,1968,p. 1704 - 1708.

5
[ 459-73-4 ]
[ 100-46-9 ]
[ 39796-52-6 ]

References: [1]Chemical and pharmaceutical bulletin,1973,vol. 21,p. 422 - 427.

6
[ 5781-53-3 ]
[ 39796-52-6 ]
[ 96042-88-5 ]

References: [1]Tetrahedron,1984,vol. 40,p. 5143 - 5152.

7
[ 824-72-6 ]
[ 39796-52-6 ]
C₂₄H₂₇N₄O₃P [ No CAS ]

References: [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 9,p. 209 - 220.

8
[ 39796-52-6 ]
C₈H₁₃NO₅ [ No CAS ]
2-Acetylamino-N-(benzylcarbamoyl-methyl)-propionamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 567 - 574.

9
[ 19811-52-0 ]
[ 39796-52-6 ]

Yield	Reaction Conditions	Operation in experiment
94.5%		N^Benzylglycinamide; Carbamic acid, [2-oxo-2-[(phenylmethyl)amino]ethyl]-, 1,1-dimethylethyl ester (1.25g, 12.62mmol) was dissolved in DCM (6mL) and TFA (5mL) was added. The reaction mixture was stirred at rt for 2h. The mixture was concentrated and diluted with EtOAc and washed with saturated aqueous K2CO3. The organic layer was dried with Na2SO4, filtered and evaporated affording the title compound (0.73g, 94.5%). 1H NMR (500MHz, CDCl3): δ 1.48 (bs, 2H), 3.38 (s, 2H), 4.46 (d, 2H), 7.26-7.35 (m, 5H), 7.64 (bs, IH); 13C NMR (125MHz, CDCl3): 543.24, 45.00, 127.65, 127.99, 128.90, 138.66, 172.93; Mass Spectrum: M+H+ 165
79%	With trifluoroacetic acid; at 20℃; for 3.5h;	To 126 (0.93 g, 3.5 mmol) obtained as mentioned above was added TFA (7 mL) and the mixture was stirred at room temperature for 3.5 hr. The reaction solution was concentrated under reduced pressure. The obtained residue was purified by moderate-pressure silica gel column chromatography (aminesilica gel 30 g, ethyl acetate/methylene chloride=10/90-95/5) to give 127 (457 mg, 2.78 mmol, yield 79%) as a light yellow liquid.
79%	With trifluoroacetic acid; at 20℃; for 3.5h;	To 126 (0.93 g, 3.5 mmol) obtained as mentioned above was added TFA (7 mL) and the mixture was stirredat room temperature for 3.5 hr. The reaction solution was concentrated under reduced pressure. The obtained residuewas purified by moderate-pressure silica gel column chromatography (aminesilica gel 30 g, ethyl acetate/methylenechloride=10/90 - 95/5) to give 127 (457 mg, 2.78 mmol, yield 79%) as a light yellow liquid.

29%		Method #6 2-Amino-N-benzylacetamide To a solution of N-benzyl-2-(tert-butoxycarbonylamino)acetamide (Method #5, 1.18 g, 4.47 mmol) in dichloromethane (6 ml) at 0 C. was added dropwise, trifluoroacetic acid (2.4 ml) and the resulting solution allowed to stir warming to room temperature overnight.The reaction mixture was neutralised by addition of saturated sodium bicarbonate solution and extracted with dichloromethane.The combined organic phases were dried over magnesium sulphate, filtered, concentrated and purified by bond-elute SCX column chromatography (eluent: methanol/dichloromethane (1:1) then methanol/dichloromethane (1:1)/ammonia 5%) to afford the title compound as an oil (215 mg, 29%). NMR: (CDCl3): 7.2 (6H, m), 4.4 (1.4H, d), 4.3 (0.6H, d), 3.4 (2H, br); m/z 165.17
3.2 g	With hydrogenchloride; In water; ethyl acetate; for 18h;	Compound 4 To a solution of Compound 1 (10 g, 57 itimol) in THF (100 mL) was added 1 , 1 ' -carbonyldiimidazole (CDI) (11.1 g, 68.5 mmol) at room temperature, and the mixture was stirred for 30 minutes. Compound 2 (7.34 g, 68.5 mmol) was then added and stirred overnight (about 18 hours) . The solvent was evaporated and the residue was dissolved in ethyl acetate (EA; 400 mL) to which was added 4 HCl/MeOH (50 mL) , and the resulting admixture was stirred overnight (about 18 hours) . The resulting white solid was filtered and suspended in EA, washed with aq.NaHC03 and concentrated to afford product as white solid (3.2 g, 34% yield, as confirmed by NMR) . 1H-NMR (400 MHz, CDC13) : 3.41 (s, 3H) ; 4.48 (d, J = 6.0 Hz, 2H) ; 7.26-7.36 (m, 5H) ; 7.57 (br, s, 1H) .
	With trifluoroacetic acid; In dichloromethane; at 20℃; for 24h;	General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH•H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.

References: [1]Tetrahedron,1984,vol. 40,p. 5143 - 5152.
[2]Patent: WO2006/73366,2006,A1 .Location in patent: Page/Page column 197.
[3]Acta poloniae pharmaceutica,2007,vol. 64,p. 127 - 137.
[4]Organic Letters,2013,vol. 15,p. 2830 - 2833.
[5]Patent: US2020/165194,2020,A1 .Location in patent: Paragraph 0185; 0187.
[6]Patent: EP3804707,2021,A1 .Location in patent: Paragraph 0200; 0202.
[7]Patent: US2003/232875,2003,A1 .Location in patent: Page 51.
[8]Organic Letters,2010,vol. 12,p. 2718 - 2721.
[9]Journal of the American Chemical Society,2011,vol. 133,p. 15316 - 15319.
[10]Patent: WO2014/11917,2014,A2 .Location in patent: Page/Page column 181.
[11]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3732 - 3735.
[12]Molecules,2017,vol. 22.

10
[ 39796-52-6 ]
[ 108-24-7 ]
[ 69753-67-9 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 567 - 574.

11
[ 39796-52-6 ]
[ 4755-77-5 ]
[ 96042-84-1 ]

References: [1]Tetrahedron,1984,vol. 40,p. 5143 - 5152.

12
[ 39796-52-6 ]
[ 2524-64-3 ]
(Benzylcarbamoyl-methyl)-phosphoramidic acid diphenyl ester [ No CAS ]

References: [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 9,p. 209 - 220.

13
[ 39796-52-6 ]
[ 159780-58-2 ]
[ 1027551-78-5 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1112 - 1124.

14
[ 39796-52-6 ]
[ 191405-26-2 ]
(S)-2-[(Benzylcarbamoyl-methyl)-thiocarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 3808 - 3809.

15
[ 39796-52-6 ]
[ 191405-20-6 ]
{(S)-1-[(Benzylcarbamoyl-methyl)-thiocarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 3808 - 3809.

16
[ 39796-52-6 ]
[ 191405-23-9 ]
{(S)-1-[(Benzylcarbamoyl-methyl)-thiocarbamoyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 3808 - 3809.

17
[ 39796-52-6 ]
[1-Benzyloxymethyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
{(S)-1-[(Benzylcarbamoyl-methyl)-thiocarbamoyl]-2-benzyloxy-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
{(R)-1-[(Benzylcarbamoyl-methyl)-thiocarbamoyl]-2-benzyloxy-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 3808 - 3809.

18
[ 6000-43-7 ]
[ 100-46-9 ]
[ 39796-52-6 ]