Trifluoroacetic acid → HCID 131713073, compound

HRID 435477Notes

Reaction equation

HRID 435477 reaction equation
Cl.[OH:2][CH:3]([CH2:9][C:10](=[O:12])[O-:11])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].[CH2:13]([C:17]1[CH:22]=[CH:21][C:20](CC([Cl:26])=O)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].[C:27](O)([C:29](F)(F)F)=[O:28]>>[ClH:26].[CH2:13]([C:17]1[CH:18]=[CH:19][C:20]([CH:4]([N+:5]([CH3:8])([CH3:6])[CH3:7])[C:3]([C:27](=[O:28])[CH3:29])([CH2:9][C:10](=[O:11])[O-:12])[OH:2])=[CH:21][CH:22]=1)[CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochlorideHCID 124225774-(2-Methylpropyl)benzeneacetyl chloride

Product 1

HCID 131713073HCID 131713073, compoundYield 65%

Procedure

5.5 g (0.028 moles) of carnitine hydrochloride are dissolved in 9 mls of CF3COOH, and to the solution an excess (20 mls) of p-isobutylphenyl acetyl chloride is added and the mixture is kept under stirring at 40°-45° C. for 4-5 hours. At the end of this period of time the mixture is partitioned with H2O--CHCl3, the organic phase is discarded and the aqueous phase is concentrated at reduced pressure at a bath temperature of about 50° C. A gelatinous raw material is obtained which is crystallized with isopropanol, the precipitate thus obtained is filtered, rapidly washed with ether because of its hygroscopicity, and dried under vacuum at a temperature not exceeding 50° C.; 6.8 g of a product are obtained (yield 65%) having the following characteristics:

Workup

  1. customAt the end of this period of time the mixture is partitioned with H2O--CHCl3
  2. concentrationthe aqueous phase is concentrated at reduced pressure at a bath temperature of about 50° C
  3. customA gelatinous raw material is obtained which
  4. customis crystallized with isopropanol
  5. customthe precipitate thus obtained
  6. filtrationis filtered
  7. washrapidly washed with ether because of its hygroscopicity
  8. customdried under vacuum at a temperature not
  9. customexceeding 50° C.

Sources & evidence

ORD record
ord-c00e89de665b42b89f55f3169f19b5ff
Source dataset
uspto-grants-1983_08
Patent number
US04401827

Reaction notes

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