Methanol → HCID 23401648, compound

HRID 1063963Notes

Reaction equation

HRID 1063963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[Cl:32])[C@H:12]([CH3:24])[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][S:17][CH:16]2CC(O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-:33].[K+].[CH3:35][OH:36]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[Cl:32])[C@H:12]([CH3:24])[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][S:17][CH:16]2[C:35]([OH:36])=[O:33])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 23401649HCID 23401649, compound

Product 1

HCID 23401648HCID 23401648, compoundYield 66%

Procedure

To a stirring solution of 4-chloro-N-(2,5-dichlorophenyl)-N-(3-(2-carboxymethyl-3-thiazolidinyl)-1(R)-methylpropyl)benzenesulfonamide (109 mg, 0.203 mmol) in methanol (20 mL) was added 50% aqueous KOH (1.0 mL) and the mixture was stirred at room temperature for 18 hours. The solvent was removed and the crude mixture was dissolved in CH2Cl2 and washed with 1N HCl. The CH2Cl2 layer was dried over Na2SO4 and evaporated to give crude product. Purification was performed over silica gel using 5-10% methanol in CH2Cl2 with 0.5% NH4OH to afford 4-chloro-N-(2,5-dichlorophenyl)-N-(3-(2-carboxy-3-thiazolidinyl)-1(R)-methylpropyl)benzenesulfonamide as a beige foam in 66% yield. IR (KBr) 1467, 1351, 1167, 1094, 753, 622 cm−1; MS (ESI+), 523 (M+H)+.

Workup

  1. customThe solvent was removed
  2. dissolutionthe crude mixture was dissolved in CH2Cl2
  3. washwashed with 1N HCl
  4. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  5. customevaporated
  6. customto give crude product
  7. customPurification

Sources & evidence

ORD record
ord-84f3cbc272444add85c33b1b8bcf62d2
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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