Potassium Hydroxide → 2-tert-butyl hydrogen (2RS,4SR,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate

HRID 725855Notes

Reaction equation

HRID 725855 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:36])[NH:10][CH2:11][C:12]([N:14]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]([C:25]([O:27]C)=[O:26])[CH2:16][CH:15]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:13])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>O.CO>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:36])[NH:10][CH2:11][C:12]([N:14]2[CH:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:17]([C:25]([OH:27])=[O:26])[CH2:16][CH:15]2[C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 867519032-tert-butyl 4-methyl (2RS,4RS,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate

Product 1

HCID 867519022-tert-butyl hydrogen (2RS,4SR,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylateYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The reaction is carried out in a way analogous to that described in Example 3, but from 1.6 g of 2-tert-butyl 4-methyl (2RS,4RS,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate and 0.18 g of potassium hydroxide in 20 cm3 of distilled water and 60 cm3 of methanol. After treatment, there is obtained 0.7 g of 2-tert-butyl hydrogen (2RS,4SR,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2,4-dicarboxylate, melting at 160° C.

Sources & evidence

ORD record
ord-43700cb820e64f84a1214b00afca4401
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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