Ethylamine → 1-[2-(R)-(3-Ethyl-ureido)-3-(4-methoxyphenyl)-propionyl]-pyrrolidin-2-(S)-carboxylic acid benzyl ester

HRID 2304344Notes

Reaction equation

HRID 2304344 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:30])[C@H:17]([N:27]=[C:28]=[O:29])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([NH2:33])[CH3:32]>ClCCl>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:30])[C@H:17]([NH:27][C:28]([NH:33][CH2:31][CH3:32])=[O:29])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 57078930HCID 57078930, compound

Product 1

HCID 536909371-[2-(R)-(3-Ethyl-ureido)-3-(4-methoxyphenyl)-propionyl]-pyrrolidin-2-(S)-carboxylic acid benzyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[2-(R)-Isocyanato-3-(4-methoxyphenyl)-propionyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester (0.60 g) was dissolved under nitrogene in 20 mL of dichloromethane and ethyl amine was allowed to pass through at-20° C. for 5 minutes. The mixture was kept stirring for 16 h. The volatiles were pumped off and the remaining residue was purified by silica chromatography (dichloromethane/methanol 80/20) to give 0.29 g (42%) of the title compound as a colorless oil. (+)-APCI-MS: 454(MH−).

Workup

  1. custom20° C.
  2. customfor 5 minutes
  3. customthe remaining residue was purified by silica chromatography (dichloromethane/methanol 80/20)

Sources & evidence

ORD record
ord-886852042ba144ae98b71fbcc32234fc
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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