Potassium Hydroxide → HCID 178525928, compound

HRID 1596617Notes

Reaction equation

HRID 1596617 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:11][C@H:10]([N:12]([OH:26])[C:13]([NH:15]S(C3C=CC(C)=CC=3)(=O)=O)=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.[CH2:27]1[CH2:31][O:30]CC1.C[OH:33].[OH-].[K+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][C@H:10]([N:12]([OH:26])[C:13](=[O:14])[NH:15][CH2:27][C:31]([OH:33])=[O:30])[CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 178427618HCID 178427618, compound

Product 1

HCID 178525928HCID 178525928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the compound prepared in Example 71, above (1.03 g, 3.32 mmol), in a THF/MeOH (5 ml/5 ml) solution was added dropwise KOH (0.285 g, 4.32 mmol) in H2O (7 ml). After stirring overnight, the volatiles were removed in vacuo, an Et2O/H2O (40 ml/30 ml) mixture was added, the aqueous layer was separated and acidified with 10% aqueous HCl and the whole was extracted with ethyl acetate (2×50 ml), washed with water and brine, then dried over MgSO4 and evaporated in vacuo. The resulting solid was triturated with an Et2O/n-hexane mixture to afford 0.74 g of desired product as a colorless solid, m.p. 137-139° C. (dec.).

Workup

  1. customthe volatiles were removed in vacuo
  2. additionan Et2O/H2O (40 ml/30 ml) mixture was added
  3. customthe aqueous layer was separated
  4. extractionthe whole was extracted with ethyl acetate (2×50 ml)
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe resulting solid was triturated with an Et2O/n-hexane mixture

Sources & evidence

ORD record
ord-52f28271b44a45689be8cbee6d37d6c0
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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