Alanine ethylamide → tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-3-{[(1S)-2-(ethylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxypropylcarbamate

HRID 14013Notes

Reaction equation

HRID 14013 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:22][C@@H:23]([CH3:29])[C:24]([NH:26][CH2:27][CH3:28])=[O:25]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:22][C@@H:23]([CH3:29])[C:24]([NH:26][CH2:27][CH3:28])=[O:25]

Participants

3

Reactant 2

HCID 7128993Alanine ethylamideHCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate

Product 1

HCID 86585850tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-3-{[(1S)-2-(ethylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxypropylcarbamate

Procedure

Following the general procedure of EXAMPLEs 4 and 14-164 and making non-critical variations and reacting tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3) with (2S)-2-amino-N-ethylpropanamide (VI), the title compound is obtained.

Sources & evidence

ORD record
ord-cb125848e80d43b083309489b8813dff
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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