Ethyl chloroformate → N-Carboethoxy-N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester

HRID 1609203Notes

Reaction equation

HRID 1609203 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH:27]([CH3:29])[CH3:28])[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:30])[C@H:10]([CH:27]([CH3:28])[CH3:29])[N:11]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 11112111(2S)-2-(2'-Cyano-4-biphenylylmethylamino)-3-methylbutyric acid benzyl ester

Product 1

HCID 54551475N-Carboethoxy-N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.0 g of N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine benzyl ester are dissolved in 150 ml of chloroform and treated with 8.2 ml of diisopropylethylamine at 0°. 2.4 ml of ethyl chloroformate are added and the mixture is heated to reflux for 3 hours. The reaction mixture is washed with 0.1M hydrochloric acid and brine, dried and concentrated. Amorphous product. TLC (system N3) Rf : 0.45.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 3 hours
  3. washThe reaction mixture is washed with 0.1M hydrochloric acid and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ce6d76dd4094b19bc44e059ea9dcb60
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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