Dicyclohexylcarbodiimide → HCID 86751898, compound

HRID 725853Notes

Reaction equation

HRID 725853 reaction equation
[C:1]([CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][CH:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:4]1)#[N:2].[CH3:21][C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:35])[NH:30][CH2:31][C:32](O)=[O:33])[CH:25]=[CH:26][CH:27]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([CH:3]1[CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:6]([C:32](=[O:33])[CH2:31][NH:30][C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[CH:23]=2)=[O:35])[CH:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 86751899HCID 86751899, compound

Product 1

HCID 86751898HCID 86751898, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction is carried out in a way analogous to that described in Example 2B, but from 1 g of tert-butyl (2RS,4RS,5SR)-4-cyano-5-phenylpyrrolidine-2-carboxylate, 0.76 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 0.76 g of N,N'-dicyclohexylcarbodiimide in 50 cm3 of acetonitrile. After treatment, there are obtained 1.2 g of tert-butyl (2RS,4RS,5SR)-4-cyano-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate, melting at 150° C.

Sources & evidence

ORD record
ord-edfcc80139ad4cd9974a8c53bfe37c51
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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