Lithium Hydroxide → HCID 19382503, compound

HRID 2400198Notes

Reaction equation

HRID 2400198 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][S:6][CH:7]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Li+].[OH-]>C1COCC1.CO>[C:11]1([CH2:10][CH2:9][CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:39])[C:35]([F:36])([F:37])[F:38])=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)[S:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67780360HCID 67780360, compound

Product 1

HCID 19382503HCID 19382503, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 300 mg of the product from Step 5 and 1.5 mL of 1M LiOH in 12 mL of 5:1 THF/MeOH was stirred for 12 hrs. at r.t. The reaction mixture was then treated with 10 mL of PH-7 buffer and extracted with EtOAc (50 mL). The extract was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography eluted with 2:1 Hexane/EtOAc containing 1% AcOH to give 240 mg of the title compound.

Workup

  1. customat r.t
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluted with 2:1 Hexane/EtOAc containing 1% AcOH

Sources & evidence

ORD record
ord-16003a5219f948029607f1b992649868
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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