Potassium Hydroxide → HCID 59505350, compound

HRID 1253659Notes

Reaction equation

HRID 1253659 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([O:26]C)=[O:25])[CH:22]=2)[CH2:17][CH2:16]1)(=[O:13])=[O:12]>C(O)C.O>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([OH:26])=[O:25])[CH:22]=2)[CH2:17][CH2:16]1)(=[O:12])=[O:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59505295HCID 59505295, compound

Product 1

HCID 59505350HCID 59505350, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

KOH (1 mol/l aq) (2 eq.) was added to a suspension of (R)-methyl 3-(2,3-dichlorophenyl-sulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (C-06) (0.85 mmol, 1 eq.) in a mixture of ethanol (4.9 ml) and water (1.1 ml). The reaction mixture was stirred at room temperature overnight. Ethanol was removed in vacuo and the aqueous residue was diluted with diethyl ether and dist. water. The phases were separated and the aqueous phase was acidified to pH 3 with 1N HCl and extracted 4× with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated to obtain the desired product (F-06). Yield: 61%

Workup

  1. customEthanol was removed in vacuo
  2. additionthe aqueous residue was diluted with diethyl ether and dist
  3. customThe phases were separated
  4. extractionextracted 4× with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-036620d7015640fb90ccbd211d2432e4
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

Loading…