Hydrochloric Acid → HCID 53879662, compound

HRID 1816729Notes

Reaction equation

HRID 1816729 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O.O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 54308849HCID 54308849, compound

Product 1

HCID 53879662HCID 53879662, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (S)-4-[4-[2-(tert-butoxycarbonylamino)-3-cyclohexylpropyloxy]phenyl]benzoate (0.28 g) in a mixed solvent of methanol (14 ml) and tetrahydrofuran (3 ml) was treated with 1N-sodium hydroxide aqueous solution, and the mixture was refluxed for 16 hours. After cooling, water was added to the mixture, and the acidity of the mixture was adjusted to pH 1 with 1N-hydrochloric acid. The resulting precipitate was filtered, washed with water and dried under reduced pressure to give (S)-4-[4-[2-(tert-butoxycarbonylamino)-3-cyclohexylpropyloxy]phenyl]benzoic acid (222 mg) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureAfter cooling
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1c1c830312c1461abb758542e6cca82e
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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