Reaction equation
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([OH:10])=[O:9])([CH3:4])[CH3:3].[Cl-].[CH2:13]([C:17]1[CH:22]=[CH:21][C:20](C(C)C([Cl:26])=O)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15]>C(O)(C(F)(F)F)=O>[ClH:26].[CH2:13]([C:17]1[CH:18]=[CH:19][C:20]([CH:5]([N+:2]([CH3:3])([CH3:4])[CH3:1])[C:6]([C:8](=[O:9])[CH2:7][CH3:6])([CH2:7][C:8](=[O:10])[O-:9])[OH:11])=[CH:21][CH:22]=1)[CH:14]([CH3:16])[CH3:15]Participants
Procedure
4.95 g (0.025 moles) of D,L-carnitine hydrochloride are dissolved in 8 mls of CF3COOH, and to the solution an excess (16 mls) of p-isobutylphenyl-alpha-methyl acetyl chloride is added and the mixture is kept under stirring at a temperature of 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 whereas the aqueous phase is concentrated under 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 hydroscopicity, and dried under vacuum at a temperature not exceeding 50° C.; 6.3 g of a product are obtained (yield 65%) having the following characteristics:
Workup
- customAt the end of this period of time, the mixture is partitioned with H2O--CHCl3
- concentrationis concentrated under reduced pressure at a bath temperature of about 50° C
- customA gelatinous raw material is obtained which
- customis crystallized with isopropanol
- customThe precipitate thus obtained
- filtrationis filtered
- washrapidly washed with ether because of its hydroscopicity
- customdried under vacuum at a temperature not
- customexceeding 50° C.
Sources & evidence
- ORD record
- ord-76ef5ee9ab87465a92aad006b091e810
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04401827
Linked notes
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