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

HRID 1106999

Reaktionsgleichung

Reaktionsgleichung von HRID 1106999
[ClH:1].C1(CNCC(N(CC2C=CC=CC=2)[C@H](C2C=CC=CC=2)C)=O)C=CC=CC=1.C[C@@H](C1C=CC=CC=1)NCC1C=CC=CC=1.[O:45]=[C:46]([N:56]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C@H:57]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH3:58])[CH2:47][NH:48][C:49](=[O:55])[O:50]C(C)(C)C>>[ClH:1].[O:45]=[C:46]([N:56]([CH2:65][C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)[C@H:57]([C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)[CH3:58])[CH2:47][NH:48][C:49](=[O:50])[OH:55]

Komponenten

4

Edukt 3

HCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 21968351tert-butyl N-{2-oxo-2-{(phenylmethyl){1(S)-phenylethyl}amino}ethyl}carbamateHCID 23390399HCID 23390399, Verbindung

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe Boc group was removed

Quellen und Nachweise

ORD-Eintrag
ord-d4ebbc2ebbaa4982b6a43b6dd6ebc83b
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057451

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