Carbamate → N-{2-oxo-2-{(phenylmethyl)(1(S)-phenylethyl}amino}ethyl}carbamate hydrochloride

HRID 1699755Notes

Reaction equation

HRID 1699755 reaction equation
[ClH:1].C1(CN[CH2:10][C:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])=[O:12])C=CC=CC=1.C[C@@H](C1C=CC=CC=1)NCC1C=CC=CC=1.[C:45](=[O:48])([O-:47])[NH2:46]>>[ClH:1].[O:12]=[C:11]([N:13]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])[CH2:10][NH:46][C:45](=[O:47])[OH:48]

Participants

4

Reactant 3

HCID 276CarbamateHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 23390399HCID 23390399, compound

Product 1

HCID 70150879N-{2-oxo-2-{(phenylmethyl)(1(S)-phenylethyl}amino}ethyl}carbamate hydrochloride

Procedure

2-(phenylmethyl)amino-N-phenylmethyl-N-{1(S)-phenylethyl}acetamide hydrochloride: By following the procedure of Example 1(a) but replacing dibenzylamine with α(S)-methyl-N-(phenylmethyl)benzene methanamine, ((S)-N-benzyl-α-methylbenzylamine, Oxford Asymmetry Ltd., Abingdon Oxon, UK), tert-butyl N-{2-oxo-2-{(phenylmethyl)1(S)-phenylethyl}amino}ethyl}carbamate was made. The Boc group was removed following the procedure of Example 1(b) to give N-{2-oxo-2-{(phenylmethyl)(1(S)-phenylethyl}amino}ethyl}carbamate hydrochloride, which was subjected to reductive amination with benzaldehyde according the procedure of R. F. Borch, Org. Synth., 1972, 52, 124, to give 2-(phenylmethyl)amino-N-phenylmethyl-N-{1(S)-phenylethyl}acetamide hydrochloride.

Workup

  1. customThe Boc group was removed

Sources & evidence

ORD record
ord-639535b9d35c4825b09def000e72beec
Source dataset
uspto-grants-2002_02
Patent number
US06348477B1

Reaction notes

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