Methanol → (2S,4R,5R)-3-{3-[2-(4-benzyl-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid

HRID 725859Notes

Reaction equation

HRID 725859 reaction equation
COC(CS[C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:41])[NH:15][CH2:16][C:17]([N:19]2[CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:22]([C:30](OC)=O)[CH2:21][CH:20]2[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:18])[CH:10]=[CH:11][CH:12]=1)=O.[OH-:42].[K+].[CH3:44][OH:45]>O>[CH2:30]([C@H:22]1[C@H:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:19]([C:17](=[O:18])[CH2:16][NH:15][C:14](=[O:41])[NH:13][C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:44]([OH:45])=[O:42])[C@H:20]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:21]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 867519102-tert-butyl 4-methyl (2RS,4RS,5SR)-1-{2-[3-(3-(methoxycarbonylmethylthio)phenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate

Product 1

HCID 86751893(2S,4R,5R)-3-{3-[2-(4-benzyl-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A The reaction is carried out in a way analogous to that described in Example 3, but from 2.6 g of 2-tert-butyl 4-methyl (2RS,4RS,5SR)-1-{2-[3-(3-(methoxycarbonylmethylthio)phenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate and 0.5 g of potassium hydroxide in a mixture of 15 cm3 of distilled water and 50 cm3 of methanol. After treatment, there are obtained 1.8 g of 2-tert-butyl hydrogen (2RS,4RS,5SR)-1-{2-[3-(3-(carboxymethylthio)phenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate [Rf =0.1; eluent: methylene chloride/methanol (90/10)].

Sources & evidence

ORD record
ord-4eb36e68a7434b019d31d272e734a919
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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