Tetrahydrofuran → HCID 67524278, compound

HRID 898862Notes

Reaction equation

HRID 898862 reaction equation
[O:1]=[C:2]1[O:7][CH2:6][C@H:5]2[C@:3]1([NH:14][S:15]([C:18]1[S:19][C:20]([C:23]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[O:25][N:24]=3)=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C@H:4]2[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O[Li].O.C1C[O:38]CC1>O>[OH:7][CH2:6][C@@H:5]1[C@H:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@:3]1([NH:14][S:15]([C:18]1[S:19][C:20]([C:23]2[CH:27]=[C:26]([C:28]([F:29])([F:31])[F:30])[O:25][N:24]=2)=[CH:21][CH:22]=1)(=[O:16])=[O:17])[C:2]([OH:38])=[O:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67524799HCID 67524799, compound

Product 1

HCID 67524278HCID 67524278, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5-(5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-sulfonic acid [(1R*,5R*,6R*)-2-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-1-yl]-amide (53 mg, 11 mmol) were added LiOH—H2O (11 mg, 0.27 mmol), 1 mL of THF and 0.5 mL of water. After stirring overnight at room temperature, the reaction mixture was concentrated, diluted with water (2 mL), and acidified to pH 4 with 2N KHSO4. The product was extracted with EtOAc, washed with water (×2), brine and dried over Na2SO4. After concentrating, the product was precipitated from dichloromethane/hexane to afford the desired product as a white solid (46 mg, 86% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water (2 mL)
  3. extractionThe product was extracted with EtOAc
  4. washwashed with water (×2), brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrating
  7. customthe product was precipitated from dichloromethane/hexane

Sources & evidence

ORD record
ord-f4e4619a162c422fb1007aeb91be290f
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

Loading…