Diethyl Ether → HCID 88333694, compound

HRID 1599520Notes

Reaction equation

HRID 1599520 reaction equation
[C:1]([OH:17])(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].S(Cl)([Cl:20])=O.O[C@H:23]([CH2:29][C:30](=[O:32])[O-:31])[CH2:24][N+:25]([CH3:28])([CH3:27])[CH3:26].C(OCC)C>ClC(Cl)(Cl)C(O)=O>[Cl-:20].[C:30]([CH2:29][C@@H:23]([O:16][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:24][N+:25]([CH3:28])([CH3:27])[CH3:26])([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10917(-)-CarnitineHCID 13849Pentadecanoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 88333694HCID 88333694, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6421Trichloroacetic AcidSolvent

Procedure

After a mixture of n-pentadecanoic acid (25 g, 103 mmol) and thionyl chloride (3.15 g, 26.5 mmol) was stirred for 3 hours at 75° to 80° C., a solution of L-carnitine (4.27 g, 26.5 mmol) in 25 g of trichloroacetic acid was added at 60° C. The resulting mixture was stirred for 3 hours at 80° C. under argon atmosphere and then poured into stirred 100 ml of diethyl ether. The precipitates were collected by filtration, washed with diethyl ether and then dried to give 11.8 g of a crude desired product as a colorless solid. 11.8 g of the crude product was recrystallized from isopropanol to provide 9.38 g of (R)-(3-carboxy-2-pentadecanoyloxypropyl)trimethylammonium chloride as colorless needles.

Workup

  1. stirringThe resulting mixture was stirred for 3 hours at 80° C. under argon atmosphere
  2. additionpoured
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with diethyl ether
  5. customdried
  6. customto give 11.8 g of a crude desired product as a colorless solid
  7. custom11.8 g of the crude product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-cde6a470306e47cf835796368220c45a
Source dataset
uspto-grants-1998_04
Patent number
US05741816

Reaction notes

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