HCID 22644724, compound → HCID 22644742, compound

HRID 2084877Notes

Reaction equation

HRID 2084877 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:26])[C:16]2([C:22]([O:24]C)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]>CO.C1COCC1.[OH-].[Na+]>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH3:26])[C:16]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:13])=[O:14])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 1

HCID 22644724HCID 22644724, compound

Product 1

HCID 22644742HCID 22644742, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]cyclohexanecarboxylate (4.6 g, 12.1 mmol) in methanol:THF (4:1, 100 ml), 10 N sodium hydroxide (15 ml) was added at room temperature. The reaction was stirred for 16 h and evaporated to dryness in vacuo and the residue was dissolved in 100 mL water. The pH was adjusted to 1 with 5N hydrochloric acid solution and the mixture was extracted with chloroform, washed with water, dried and concentrated to give 1-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]cyclohexanecarboxylic acid as a yellow solid. Yield: 4 g (88%); mp 124-6° C. Electrospray Mass Spec 364(M−H)−.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in 100 mL water
  3. extractionthe mixture was extracted with chloroform
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a66351859a4b440e936999c581b7dc9c
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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