Water → (S)-2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one

HRID 622377Notes

Reaction equation

HRID 622377 reaction equation
Br[C@H:2]([CH:16]([CH3:18])[CH3:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:7]=1[OH:15])=[O:4].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:16]([C@H:2]1[C:3](=[O:4])[NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:7]=2[O:15]1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 6932486(R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol

Product 1

HCID 7210282(S)-2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-oneYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol (18.5 g) in dimethylformamide (120 ml) was treated with powdered potassium carbonate (9.75 g) at room temperature for 3 hours. Dilution with water gave crystals, which were recrystallized from 2-propanol to yield (S)-2,8-diisopropyl-2H-1,4-benzoxazin-3(4H)-one as colorless prisms (11.0 g, 80.3%), mp 151°-152° C., [α]D23 -5.6° (c=1.0, MeOH).

Workup

  1. customwere recrystallized from 2-propanol

Sources & evidence

ORD record
ord-f6e5f76c6c214c99bd6bd590bbd78c10
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

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