Benzoyl chloride → HCID 13649256, compound

HRID 1200151Notes

Reaction equation

HRID 1200151 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]([NH:17][C:18](=[O:30])[C@@H:19]([NH2:29])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[CH3:16][C:9]([NH:17][C:18](=[O:30])[C@@H:19]([NH:29][C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:8])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471Triethylamine2×HCID 68114567HCID 68114567, compound

Product 1

HCID 13649256HCID 13649256, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.2 g of an oily substance [which had been obtained by the treatment of the (2S)-N-(α,α-dimethylbenzyl)-3-benzyloxy-2-aminopropionamide trifluoroacetate (prepared as described in Preparation 5) with triethylamine] were dissolved, together with 1.5 g of triethylamine, in 150 ml of methylene chloride. 1.5 g of benzoyl chloride was dropped onto this solution in an ice bath, and the reaction solution was stirred for 30 minutes, after which the methylene chloride layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off and recrystallization of the residue from a mixture of diethyl ether and hexane gave 4.1 g of the title compound melting at 88°-90° C.

Workup

  1. customafter which the methylene chloride layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customrecrystallization of the residue
  6. additionfrom a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-5059cfbaad654e53a41010ee2649a41e
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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