2-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol → (4S,5R)-2-(6-tert-Butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid ((S)-3,4-dihydroxy-butyl)-amide

HRID 1894502Notes

Reaction equation

HRID 1894502 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32](Cl)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:35][CH2:36][CH3:37])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][CH2:40][C@H:41]([OH:44])[CH2:42][OH:43].OCC[C@H]1COC(C)(C)O1>>[OH:44][C@H:41]([CH2:42][OH:43])[CH2:40][CH2:39][NH:38][C:32]([N:12]1[C@@:13]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)([CH3:24])[C@@:14]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)([CH3:16])[N:15]=[C:11]1[C:8]1[CH:9]=[N:10][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][C:7]=1[O:35][CH2:36][CH3:37])=[O:33]

Participants

4

Reactant 3

HCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-olHCID 55281176(2S)-4-aminobutane-1,2-diolHCID 57669958(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 57670151(4S,5R)-2-(6-tert-Butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid ((S)-3,4-dihydroxy-butyl)-amide

Procedure

In a manner analogous to the method described in examples 8, (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 51) was coupled with (S)-4-amino-butane-1,2-diol (prepared from (4S)-(+)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated for C33H41C12N4O4 [(M+H)+] 627.25, observed 627.2497.

Sources & evidence

ORD record
ord-e81d7c7cecc44008924e296e19ecb604
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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