Sodium Hydroxide → HCID 86587109, compound

HRID 2084866Notes

Reaction equation

HRID 2084866 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O-:18])=[O:17])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1.CO.[Cl-].[Na+].O>[C:4]([Si:1]([CH3:2])([CH3:3])[O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 86587110HCID 86587110, compound

Product 1

HCID 86587109HCID 86587109, compound

Reagents, catalysts & solvents 2

HCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tert-butyl(dimethyl)silyl(2R)-){[4-(2-butynyloxy)phenyl]sulfonyl}amino)(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)ethanoate (0.76 g, 1.24 mmol) in 8 mL of THF/methanol (1:1) was added 1 N NaOH (1.25 mL, 1.25 mmol) and the reaction was stirred at room temperature overnight. Reducing the solvent to one quarter volume, then adding brine, the aqueous layer was neutralized with 1M KHSO4 to pH˜4 and then extracted with ethyl acetate. The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to obtain 0.68 g of (2R)-{[4-(2-butynyloxy)phenyl]sulfonyl)amino)(4-{[tert-butyl-(dimethyl)silyl]oxy}cyclohexyl)ethanoic acid. Electrospray Mass Spec 494.2 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0f60445daca42a5bbc313d24d970bb7
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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