Hydrochloric Acid → HCID 20549352, compound

HRID 1659939Notes

Reaction equation

HRID 1659939 reaction equation
[F:1][C:2]([F:34])([F:33])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[O:24])=[CH:21][CH:20]=1.[OH-].[K+].C(O)C.Cl>O>[F:1][C:2]([F:33])([F:34])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:32]=[CH:31][C:22]([C:23]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 20549399HCID 20549399, compound

Product 1

HCID 20549352HCID 20549352, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.4 g. of methyl 3-{4-[15-(trifluoromethyl)pentadecylamino]benzoyl}propionate is stirred with 5.4 g. of potassium hydroxide in 100 ml. of 95% ethanol for 3 hours at reflux. The reaction mixture is cooled, diluted with 50 ml. of ethanol and 100 ml. of water, and neutralized with hydrochloric acid. The solution is cooled to room temperature and filtered. The white solid is washed with 50% aqueous ethanol and dried. The product is recrystallized from ethanol to yield 3-{4-[15-(trifluoromethyl)pentadecylamino]benzoyl}propionic acid as a white crystalline solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additiondiluted with 50 ml
  3. filtrationfiltered
  4. washThe white solid is washed with 50% aqueous ethanol
  5. customdried
  6. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-f97069d0dbf04c4e932d696ed9f85fe9
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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