Benzoyl chloride → HCID 33269723, compound

HRID 47041Notes

Reaction equation

HRID 47041 reaction equation
Br.[CH2:2]([NH:4][C:5](=[O:14])[C@H:6]([CH3:13])[NH:7][C:8](=[O:12])[C@H:9]([CH3:11])[NH2:10])[CH3:3].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH2:2]([NH:4][C:5](=[O:14])[C@H:6]([CH3:13])[NH:7][C:8](=[O:12])[C@H:9]([CH3:11])[NH:10][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86736707HCID 86736707, compound

Product 1

HCID 33269723HCID 33269723, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.35 g (0.0087 mol) of L-alanyl-L-alanine ethylamide hydrobromide were suspended in 40 ml of pyridine and 2.04 ml (0.02 mol) of benzoyl chloride were added. The mixture was then stirred for 2 hours at room temperature. The solvent was evaporated and the residue recrystallised from isopropanol to yield 1.3 g (51%) of N-benzoyl-L-alanyl-L-alanine ethylamide of melting point 237°-239° C; [α]D20 =-17.8° (c=1.01% in methanol).

Workup

  1. customThe solvent was evaporated
  2. customthe residue recrystallised from isopropanol

Sources & evidence

ORD record
ord-76a8679d83fa4ade844730dcdc517673
Source dataset
uspto-grants-1979_11
Patent number
US04176116

Reaction notes

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