Chlorocarbamate → (1r,2s)-1-{[(2s,4r)-1-[(1S)-1-((1r)-2-hydroxy-1-phenyl-ethylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

HRID 1822448Notes

Reaction equation

HRID 1822448 reaction equation
ClNC(=O)[O-].C([O:8][C:9]([C:11]1([NH:16][C:17]([CH:19]2[CH2:23][CH:22]([O:24][C:25]3[C:34]4[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=4)[N:28]=[C:27]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:26]=3)[CH2:21][N:20]2[C:43](=[O:63])[NH:44][CH:45]([C:50](=[O:62])[NH:51][CH:52]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)C[CH:53]2[OH:61])[C:46]([CH3:49])([CH3:48])[CH3:47])=[O:18])[CH2:13][CH:12]1[CH:14]=[CH2:15])=[O:10])C>>[OH:61][CH2:53][C@H:52]([NH:51][C:50]([C@@H:45]([NH:44][C:43]([N:20]1[CH2:21][C@H:22]([O:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[N:28]=[C:27]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:26]=2)[CH2:23][C@H:19]1[C:17]([NH:16][C@:11]1([C:9]([OH:10])=[O:8])[CH2:13][C@H:12]1[CH:14]=[CH2:15])=[O:18])=[O:63])[C:46]([CH3:48])([CH3:49])[CH3:47])=[O:62])[C:60]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

3

Reactant 2

HCID 22035886ChlorocarbamateHCID 684916281-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68490859(1r,2s)-1-{[(2s,4r)-1-[(1S)-1-((1r)-2-hydroxy-1-phenyl-ethylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

Procedure

The afforded compound was then reacted with the chlorocarbamate achieved from 12 as described for the preparation of 13 which gave the title compound. Purity by HPLC >95%. M+H+750.3.

Sources & evidence

ORD record
ord-f9d0b3ad9e154fc6b944d47410aad734
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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