Water → HCID 11540421, compound

HRID 490071Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@:12]([CH2:22][OH:23])([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1.C(OCC)(=O)C.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@@:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[CH:19][CH:20]=2)([CH2:22][OH:23])[CH2:11][O:10][C:9]1([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (S)-4-hydroxymethyl-4-[2-(4-hydroxy-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (100 mg, 0.28 mmol) in DMF (5 ml) is added CsCO3 (120.5 mg, 0.37 mmol, 1.3 eq) and 1-(2-bromo-ethoxy)-3-fluoro-benzene (80.7 mg, 0.37 mmol, 1.3 eq). The reaction mixture is stirred at 85° C. for 4 hours. Ethyl acetate and water are then added, the organic layer is separated and the aqueous phase is extracted with ethylacetate (3×50 ml). The combined organic extracts are washed with brine, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (AcOEt/Hx 9:1) affords (S)-4-(2-{4-[2-(3-fluoro-phenoxy)-ethoxy]-phenyl}-ethyl)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as colorless oil.

Workup

customthe organic layer is separated
extractionthe aqueous phase is extracted with ethylacetate (3×50 ml)
washThe combined organic extracts are washed with brine
dry with materialdried over MgSO4
customevaporated to dryness
customPurification by flash chromatography (AcOEt/Hx 9:1)

Sources & evidence

ORD record: ord-308968d781994820a62b20945505f34b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528120B2

Reaction notes

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