Potassium Carbonate → (2S)-[2-(4-Fluorophenyl)-2-hydroxyethyl]methylcarbamic acid t-butyl ester

HRID 1351267Notes

Reaction equation

HRID 1351267 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:30])[CH2:9][C@@H:10]([O:18]C(=O)[C@@H](OC)C1C=CC=CC=1)[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][C@H:10]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[OH:18])[CH3:30])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86600988(2S)-methoxyphenyl acetic acid (1S)-2-(t-butoxycarbonyl-methylamino)-1-(4-fluorophenyl)ethyl ester

Product 1

HCID 69416829(2S)-[2-(4-Fluorophenyl)-2-hydroxyethyl]methylcarbamic acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (2S)-methoxyphenyl acetic acid (1S)-2-(t-butoxycarbonyl-methylamino)-1-(4-fluorophenyl)ethyl ester (the compound of Preparation Example 35) (3.6 g) in methanol (17 mL) was added potassium carbonate (1.8 g) on an ice bath. After stirring at room temperature for 30 minutes, the colorless solid that was generated by diluting with water was collected by filtration. After washing with water, and then drying by aeration, the title compound (2.35 g) was obtained as a colorless solid. The NMR data matched the racemic mixture described in Preparation Example 32.

Workup

  1. filtrationwas collected by filtration
  2. washAfter washing with water
  3. customdrying by aeration

Sources & evidence

ORD record
ord-22caf8bad319436d96570242f9afbedd
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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