Hydrochloric Acid → HCID 20198263, compound

HRID 652042Notes

Reaction equation

HRID 652042 reaction equation
[CH3:1][Si:2]([CH3:33])([CH3:32])[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][NH:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[O:23])=[CH:20][CH:19]=1.[OH-].[K+].C(O)C.Cl>O>[CH3:33][Si:2]([CH3:1])([CH3:32])[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][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 20198232HCID 20198232, compound

Product 1

HCID 20198263HCID 20198263, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.4 g. of methyl 3-[4-[14-(trimethylsilyl)tetradecylamino]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 to yield 3-[4-[14-(trimethylsilyl)tetradecylamino]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

Sources & evidence

ORD record
ord-accc9ce6d8504295b2dfd32400a04e9e
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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