Triethylamine → HCID 13385094, compound

HRID 2418185Notes

Reaction equation

HRID 2418185 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([N:16]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:17][C:18]([OH:20])=O)=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:26]([O:30][C:31](=[O:41])[C@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH2:33])([CH3:29])([CH3:28])[CH3:27].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O>[C:26]([O:30][C:31](=[O:41])[C@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:33][C:18](=[O:20])[CH2:17][N:16]([C:14](=[O:15])[C@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 13089667N-[(Benzyloxy)carbonyl]-L-alanyl-N-cyclopentylglycine

Product 1

HCID 13385094HCID 13385094, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Carbobenzoxy-L-alanyl-N-cyclopentylglycine (4 g) and L-phenylalanine tert-butyl ester (2.4 g) are dissolved in 20 ml of dimethylformamide and under ice-cooling and stirring, a solution of 1.9 g of diethyl cyanophosphate in 5 ml of dimethylformamide is added, followed by addition of 1.6 ml of triethylamine. The mixture is stirred at room temperature for 3 hours. Then, 200 ml of ice water is added and the mixture is extracted twice with 50 ml portions of ethyl acetate. The extract is washed with 1N hydrochloric acid and water and dried. The solvent is then distilled off under reduced pressure to give 6.7 g of N-carbobenzoxy-L-alanyl-N-cyclopentylglycyl-L-phenylalanine tert-butyl ester as colorless oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. extractionthe mixture is extracted twice with 50 ml portions of ethyl acetate
  4. washThe extract is washed with 1N hydrochloric acid and water
  5. customdried
  6. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-149ca6ed99814bc080085e6337b079e4
Source dataset
uspto-grants-1984_09
Patent number
US04472383

Reaction notes

Loading…