Acetic Acid → (4S)-3-[(2S,3S)-2-Azido-3-(4-fluorophenyl)butanoyl]-4-phenyl-1,3-oxazolidin-2-one

HRID 970205Notes

Reaction equation

HRID 970205 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:24])[CH2:9][C:10]([N:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][O:14][C:13]2=[O:23])=[O:11])=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].CC(C1C=C(C(C)C)C(S([N:50]=[N+:51]=[N-:52])(=O)=O)=C(C(C)C)C=1)C.C(O)(=O)C.C([O-])(=O)C.[K+]>C1COCC1>[N:50]([C@@H:9]([C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH3:24])[C:10]([N:12]1[C@@H:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][O:14][C:13]1=[O:23])=[O:11])=[N+:51]=[N-:52]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 517044Potassium AcetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 69364772(4S)-3-[(3R)-3-(4-Fluorophenyl)butanoyl]-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 86605121(4S)-3-[(2S,3S)-2-Azido-3-(4-fluorophenyl)butanoyl]-4-phenyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the product from Step B (1.18 g, 3.61 mmol) in anhydrous THF (40 mL) was added potassium hexamethyldisilazide (8.7 mL, 0.5M in toluene, 4.35 mmol) at −78° C. The resultant mixture was stirred at −78° C. for 30 min. A precooled solution of trisyl azide (1.56 g, 5.04 mmol) in THF (30 mL) was added via cannula. After 1.5 min the reaction was quenched with glacial acetic acid (0.95 mL, 16.6 mmol) and potassium acetate (1.77 g, 18.1 mmol). The cooling bath was removed, and the reaction was stirred at room temperature for 12 h. The solution was partitioned between ethyl acetate and brine. The aqueous phase was extracted with three portions of ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated in vacuo. Purification by flash chromatography (silica gel, 80:20 hexanes/ethyl acetate) afforded the desired product.

Workup

  1. customThe cooling bath was removed
  2. customThe solution was partitioned between ethyl acetate and brine
  3. extractionThe aqueous phase was extracted with three portions of ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel, 80:20 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-da85f074542a4fd08196575823219dee
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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