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

HRID 725854Notes

Reaction equation

HRID 725854 reaction equation
[C:1]([CH:4]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5]1)(=[O:3])[CH3:2].[CH3:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:36])[NH:31][CH2:32][C:33](O)=[O:34])[CH:26]=[CH:27][CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([CH:4]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]([C:33](=[O:34])[CH2:32][NH:31][C:30]([NH:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH3:22])[CH:24]=2)=[O:36])[CH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 86751901HCID 86751901, compound

Product 1

HCID 86751900tert-butyl (2RS,4RS,5SR)-4-acetyl-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylateYield 13.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction is carried out in a way analogous to that described in Example 2B, but from 4.5 g of tert-butyl (2RS,4RS,5SR)-4-acetyl-5-phenylpyrrolidine-2-carboxylate, 3.2 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 3.5 g of N,N'-dicyclohexylcarbodiimide in 50 cm3 of acetonitrile. After treatment, there is obtained 1 g of tert-butyl (2RS,4RS,5SR)-4-acetyl-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate, melting at 100° C.

Sources & evidence

ORD record
ord-39048050de854fb7a23f242e5ba18713
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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