Triethylamine → HCID 54557228, compound

HRID 1583243Notes

Reaction equation

HRID 1583243 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])[CH3:2].Br.C(N(CC)CC)C.[C:28]([O:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=1)(=[O:30])[CH3:29].C(N=C=NCCCN(C)C)C.Cl>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH:9][C:36](=[O:37])[C:35]1[CH:34]=[CH:33][C:32]([O:31][C:28](=[O:30])[CH3:29])=[CH:40][CH:39]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86740488HCID 86740488, compound

Product 1

HCID 54557228HCID 54557228, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.3 g (0.05 mol) of L-alanyl-L-phenylalanine ethyl ester·HBr was suspended in 250 ml of dichloromethane, and to this susension were added 5.1 g (0.05 mol) of triethylamine and 9 g (0.05 mol) of p-acetoxybenzoic acid, and then 9.6 g (0.05 mol) of 1-ethyl-3(3-dimethylaminopropyl)carbodiimide·HCl was added in an ice bath. This mixture was stirred for three hours, and then was washed with a 0.1% aqueous solution of Na2CO3 and with a 0.1 N HCl solution three times and then with distilled water three times, and was dried over anhydrous sodium sulfate. Dichloromethane was removed from the dried mixture under reduced pressure to obtain p-acetoxybenzoyl-L-alanyl-L-phenylalanine ethyl ester.

Workup

  1. washwas washed with a 0.1% aqueous solution of Na2CO3 and with a 0.1 N HCl solution three times
  2. dry with materialwith distilled water three times, and was dried over anhydrous sodium sulfate
  3. customDichloromethane was removed from the dried mixture under reduced pressure

Sources & evidence

ORD record
ord-f43b350b80594e6c86bf3c897b71526d
Source dataset
uspto-grants-1985_11
Patent number
US04551272

Reaction notes

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