Water → HCID 18347217, compound

HRID 2269578Notes

Reaction equation

HRID 2269578 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:9]=1[CH2:10]Br)=[O:4].[OH2:27]>CN(C=O)C>[OH:27][CH2:10][C:9]1[C:8]([C:12]2[CH:13]=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=2)=[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[S:6][C:5]=1[C:3]([OH:2])=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 54071145HCID 54071145, compound

Product 1

HCID 18347217HCID 18347217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 249 mg of the product of Step 2 in 5 mL of DMF was added 237 mg of n-Bu4NOAc. The reaction mixture was stirred at r.t. for 15 min. Water (20 mL) was added and the product was extracted with 50 mL of EtOAc. The extract was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in 4 mL of THF and 2 mL of MeOH and treated with 1 ml of 1N LiOH. After 12 h, the reaction mixture was treated with 0.2 ml of HOAc and 10 mL of brine. The product was extracted with 40 mL of EtOAc. The extract was dried over MgSO4 and concentrated in vacuo to provide 120 mg of title compound as a white solid.

Workup

  1. extractionthe product was extracted with 50 mL of EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 4 mL of THF
  5. addition2 mL of MeOH and treated with 1 ml of 1N LiOH
  6. waitAfter 12 h
  7. additionthe reaction mixture was treated with 0.2 ml of HOAc and 10 mL of brine
  8. extractionThe product was extracted with 40 mL of EtOAc
  9. dry with materialThe extract was dried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b81fc189098c4cf99bd3b6725a6fe00a
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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