1,1-Dimethylethyl (3R)-3-aminobutanoate → (r)-3-((s)-2-(4,4-Bis(trifluoromethyl)-3-(4-(3-(2-methylphenyl)ureido)-3-methoxy-benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl) acetylamino)-3-methylpropionic acid

HRID 1840624Notes

Reaction equation

HRID 1840624 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1([C:18]([F:21])([F:20])[F:19])[C:7](=[O:8])[N:6]([C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10](O)=[O:11])[C:5](=[O:17])[NH:4]1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32](=[O:44])[NH:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][C:35]=1[O:42][CH3:43].[NH2:45][C@H:46]([CH3:55])[CH2:47][C:48]([O:50]C(C)(C)C)=[O:49]>>[F:1][C:2]([F:22])([F:23])[C:3]1([C:18]([F:21])([F:20])[F:19])[C:7](=[O:8])[N:6]([C@@H:9]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:10]([NH:45][C@H:46]([CH3:55])[CH2:47][C:48]([OH:50])=[O:49])=[O:11])[C:5](=[O:17])[N:4]1[CH2:38][C:37]1[CH:40]=[CH:41][C:34]([NH:33][C:32]([NH:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH3:24])=[O:44])=[C:35]([O:42][CH3:43])[CH:36]=1

Participants

4

Reactant 3

HCID 27338261,1-Dimethylethyl (3R)-3-aminobutanoateHCID 9924523(s)-2-(4,4-Bis(trifluoromethyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetic acidHCID 111625254-(3-(2-Methylphenyl)ureido)-3-methoxybenzyl chloride

Product 1

HCID 12044603(r)-3-((s)-2-(4,4-Bis(trifluoromethyl)-3-(4-(3-(2-methylphenyl)ureido)-3-methoxy-benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl) acetylamino)-3-methylpropionic acidYield 53%

Procedure

which had been prepared from (S)-2-(4,4-bis(trifluoromethyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetic acid and 4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl chloride as described in Example 18f, and 128 mg (0.809 mmol) of tert-butyl (R)-3-aminobutanoate. After coupling, chromatographic purification over silica gel (eluent: heptane/ethyl acetate=3/2) and cleavage of the tert-butyl ester, 299 mg (53%) of the title compound were obtained.

Workup

  1. customchromatographic purification over silica gel (eluent: heptane/ethyl acetate=3/2) and cleavage of the tert-butyl ester

Sources & evidence

ORD record
ord-f074dd3d26e044e78e8ec478aca35356
Source dataset
uspto-grants-2004_01
Patent number
US06680333B2

Reaction notes

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