5-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chloride → HCID 67524799, compound

HRID 898857Notes

Reaction equation

HRID 898857 reaction equation
[NH2:1][C@:2]12[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C@H:6]1[CH2:5][O:4][C:3]2=[O:14].[F:15][C:16]([F:32])([F:31])[C:17]1[O:21][N:20]=[C:19]([C:22]2[S:26][C:25]([S:27](Cl)(=[O:29])=[O:28])=[CH:24][CH:23]=2)[CH:18]=1>N1C=CC=CC=1>[O:14]=[C:3]1[O:4][CH2:5][C@H:6]2[C@:2]1([NH:1][S:27]([C:25]1[S:26][C:22]([C:19]3[CH:18]=[C:17]([C:16]([F:15])([F:31])[F:32])[O:21][N:20]=3)=[CH:23][CH:24]=1)(=[O:28])=[O:29])[C@H:7]2[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 27775265-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chlorideHCID 67524225HCID 67524225, compound

Product 1

HCID 67524799HCID 67524799, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(1R*,5R*,6R*)-1-amino-6-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one (0.14 g, 0.74 mmol) was dissolved in 3 mL of pyridine. After cooling to 0° C., 5-(5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-sulfonyl chloride (0.31 g, 0.96 mmol) was added in one portion. The reaction mixture was warmed to room temperature and stirred overnight. After concentration, the reaction mixture was diluted with EtOAc, washed with 10% citric acid, water (×2), 5% NaHCO3 and brine and dried over Na2SO4. After concentration, the crude product was purified by column chromatography using 2:1 hexanes/EtOAc to afford 0.26 g (75%) of the desired product.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. concentrationAfter concentration
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with 10% citric acid, water (×2), 5% NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b5ef0201819e413983891e5184c5392f
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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