Hydrochloric Acid → HCID 20536523, compound

HRID 1156135Notes

Reaction equation

HRID 1156135 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([O:10]C)=[O:9])=[O:5].[OH-].[K+].C(O)C.Cl>O>[F:1][C:2]1[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:13]=[CH:12][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 20536526HCID 20536526, compound

Product 1

HCID 20536523HCID 20536523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.4 g. of methyl 3-[2-fluoro-4-(hexadecylamino)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-[2-fluoro-4-(hexadecylamino)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-86b5303287e544fbbcc18dc3c3f1d2b6
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

Loading…