Benzyl Alcohol → 4-((S)-2-{[5-((S)-1-Benzyloxycarbonyl-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester

HRID 1970432Notes

Reaction equation

HRID 1970432 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:39])[C@@H:13]([NH:23][C:24]([C:26]2[CH:31]=[C:30]([OH:32])C=C(C3C=CC=CC=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:40]([O:47][C:48](=[O:52])[C@H:49](Br)[CH3:50])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Br[C@H](C)C(O)=O.C(O)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.C[N:68](C=O)C>>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:39])[C@@H:13]([NH:23][C:24]([C:26]2[CH:31]=[C:30]([O:32][C@H:49]([C:48]([O:47][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:52])[CH3:50])[N:68]([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 6992152(2R)-2-Bromopropanoic acidHCID 86609523benzyl-(R)-2-bromo-propionateHCID 178473387HCID 178473387, compound

Product 1

HCID 668547574-((S)-2-{[5-((S)-1-Benzyloxycarbonyl-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester

Procedure

To a solution of 4.00 g 4-{(S)-4-tert-Butoxycarbonyl-2-[(4-hydroxy-6-phenyl-pyridine-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 30 ml DMF were added 1.84 g (R)-2-bromo-propionic acid benzyl ester (prepared by standard benzylation procedure using (R)-2-bromopropionic acid and benzyl alcohol

Workup

  1. customprepared by standard benzylation procedure

Sources & evidence

ORD record
ord-2ef0c71c63d04173990e034f890f894d
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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