Water → (1RS,2SR)-2-amino-3-(4-tert-butylphenyl)-1-(3-chlorophenyl)propan-1-ol

HRID 1610626Notes

Reaction equation

[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][CH:10]2[CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[O:13]C(=O)[NH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>C(O)C>[NH2:11][CH:10]([CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:24][CH:23]=1)[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[OH:13]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (4RS,5SR)-4-(4-tert-butylbenzyl)-5-(3-chlorophenyl)-1,3-oxazolidin-2-one (9.50 g, 27.6 mmol) in ethanol (70 ml) was added 8N aqueous sodium hydroxide solution (17.3 ml, 138 mmol), and the mixture was stirred at 80° C. overnight. To the reaction solution was added water (20 ml) and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (8.82 g, 100%).

Workup

extractionthe mixture was extracted with ethyl acetate (50 ml×2)
washThe extract was washed with water and saturated brine
dry with materialdried (anhydrous magnesium sulfate)
customevaporated under reduced pressure
customto give the objective substance (8.82 g, 100%)

Sources & evidence

ORD record: ord-8efca38025484c179ea9446a963b5c1d
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Reaction notes

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