Butyric Acid → HCID 20446789, compound

HRID 905297Notes

Reaction equation

HRID 905297 reaction equation
Br.[CH2:2]([N:9]([CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([OH:32])[CH:26]=1)=[O:24])[CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:33]([OH:38])(=O)[CH2:34][CH2:35][CH3:36].Cl.[C:40]([Cl:45])(=[O:44])[CH2:41][CH2:42][CH3:43]>>[ClH:45].[CH2:2]([N:9]([CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:40](=[O:44])[CH2:41][CH2:42][CH3:43])=[C:27]([O:32][C:33](=[O:38])[CH2:34][CH2:35][CH3:36])[CH:26]=1)=[O:24])[CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 264Butyric AcidHCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 20446771HCID 20446771, compound

Product 1

HCID 20446789HCID 20446789, compound

Procedure

A mixture of 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-dihydroxyacetophenone hydrobromide (1.0 g.) and butyric acid (6 ml.) was saturated at room temperature with gaseous hydrogen chloride during 3 minutes. Butyryl chloride (6 ml.) was then added and the mixture was stirred at 90°-95° C. for 1.5 hours, giving a clear solution after about 5 minutes. The solution was then concentrated to half volume by evaporation under reduced pressure and the residue was diluted with ether (25 ml.) to give 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(butyryloxy)acetophenone hydrochloride as a solid precipitate (0.65 g.), m.p. 115°-117° C.

Workup

  1. customgiving a clear solution after about 5 minutes
  2. concentrationThe solution was then concentrated to half volume by evaporation under reduced pressure
  3. additionthe residue was diluted with ether (25 ml.)

Sources & evidence

ORD record
ord-e802782ca44e416f8476ec34b6ff8aae
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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