Methanol → 2-[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl) phenyl]N-tert-butyl-2-hydroxyacetamide

HRID 2075957Notes

Reaction equation

HRID 2075957 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:33][CH3:34])=[CH:11][C:12]([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)=[C:13]([CH:15]([O:23]C(=O)C)[C:16](=[O:22])[NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CO.C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]1[C:10]([O:33][CH3:34])=[CH:11][C:12]([C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)=[C:13]([CH:15]([OH:23])[C:16]([NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86647228Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

Product 1

HCID 670964872-[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl) phenyl]N-tert-butyl-2-hydroxyacetamideYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]-tert-butylcarbamoyl methyl ester (Reference example 12-1) (604 mg), a 5 mol/L aqueous solution of sodium hydroxide (1 mL) and methanol (8 mL) was stirred at room temperature for 1.5 hours. Ethyl acetate and water were added to the mixture. The separated organic layer was washed with water, an aqueous solution of sodium bicarbonate successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (552 mg).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialan aqueous solution of sodium bicarbonate successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dfc5ee8a49b47fd9b2d43567bbce7e7
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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