Hydrochloric Acid → HCID 22405886, compound

HRID 2269576Notes

Reaction equation

HRID 2269576 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:9]=1[CH2:10]Br)=[O:4].[Li+].[OH-:30].[Na+].[Cl-].Cl>C1COCC1.O.C1COCC1>[OH:30][CH2:10][C:9]1[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:14][CH:13]=2)=[C:7]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[S:6][C:5]=1[C:3]([OH:2])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 54283545HCID 54283545, compound

Product 1

HCID 22405886HCID 22405886, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 400 mg of the product of Step 6, 10 g of n-Bu4NOAcin 10 mL of THF were stirred at room temperature for 2 h. The reaction mixture was diluted with 50 mL of 3:2 THF/H2O and treated with 10 mL of 1N LiOH for 8 h. The reaction mixture was poured into a mixture of 20 mL of sat. NaCl and 10 mL of 2N HCl, and then extracted with 100 mL of EtOAc. The extract was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography and eluted with 19:1 EtOAc/AcOH to yield 250 mg of the title compound.

Workup

  1. extractionextracted with 100 mL of EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography
  5. washeluted with 19:1 EtOAc/AcOH

Sources & evidence

ORD record
ord-3c99ed31a94f44a5b3f6dba4c19b2e46
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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