Sodium Hydroxide → HCID 22644926, compound

HRID 2414587Notes

Reaction equation

HRID 2414587 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2([C:21]([O:23]C)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([NH:15][C:16]2([C:21]([OH:23])=[O:22])[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 2

HCID 14798Sodium HydroxideHCID 22644917HCID 22644917, compound

Product 1

HCID 22644926HCID 22644926, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclopentane carboxylate (5.5 g, 15.6 mmol) in methanol:THF (4:1, 100 ml) 10 N sodium hydroxide (15 ml) was added at room temperature. It was stirred for 16 h and evaporated to dryness in vacuo, the residue was dissolved in 100 mL water, pH adjusted to 7 with 5N hydrochloric acid solution. It was extracted with chloroform;methanol (3:1) washed with water, dried and concentrated to give 1-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclopentane carboxylic acid. Yield 4.5 g (86%); White solid, mp. 108-110° C. Electrospray Mass Spec 336 (M−H)−.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in 100 mL water
  3. extractionIt was extracted with chloroform
  4. washmethanol (3:1) washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-684d31dc58e04a58a2659ebce507d8ee
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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