Dicyclohexylcarbodiimide → tert-butyl (2RS,4RS,5SR)-4-dimethylcarbamoyl-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate

HRID 725852Notes

Reaction equation

HRID 725852 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:8][CH:7]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6]1)=[O:4].[CH3:24][C:25]1[CH:26]=[C:27]([NH:31][C:32](=[O:38])[NH:33][CH2:34][C:35](O)=[O:36])[CH:28]=[CH:29][CH:30]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:1][N:2]([CH3:23])[C:3]([CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]([C:35](=[O:36])[CH2:34][NH:33][C:32]([NH:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=2)=[O:38])[CH:7]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 86751897tert-butyl (2RS,4RS,5SR)-4-dimethylcarbamoyl-5-phenylpyrrolidine-2-carboxylate

Product 1

HCID 86751896tert-butyl (2RS,4RS,5SR)-4-dimethylcarbamoyl-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A The reaction is carried out in a way analogous to that described in Example 2B but from 1.7 g of tert-butyl (2RS,4RS,5SR)-4-dimethylcarbamoyl-5-phenylpyrrolidine-2-carboxylate, 1.15 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 1.15 g of N,N'-dicyclohexylcarbodiimide in 50 cm3 of acetonitrile. After treatment, there are obtained 2.2 g of tert-butyl (2RS,4RS,5SR)-4-dimethylcarbamoyl-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate, melting at 199° C.

Sources & evidence

ORD record
ord-1898a1ece6cb42239d68cdd5aa597a39
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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