Sodium Hydroxide → HCID 131727783, compound

HRID 1437947Notes

Reaction equation

HRID 1437947 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C@@H:19]4[C:23]([CH3:25])([CH3:24])[C@@:16]([CH3:26])([CH2:17][CH2:18]4)[C:15]=3[N:14]2[CH3:27])=[CH:8][CH:7]=1>CO.O1CCCC1>[CH3:27][N:14]1[C:15]2[C@@:16]3([CH3:26])[C:23]([CH3:24])([CH3:25])[C@H:19]([CH2:18][CH2:17]3)[C:20]=2[C:21](=[O:22])[N:13]1[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:28])=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57941324HCID 57941324, compound

Product 1

HCID 131727783HCID 131727783, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 M NaOH (1.1 mL, 1.1 mmol) was added to a solution of (4S,7R)-4-(1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid methyl ester (228 mg, 0.644 mmol) in methanol (0.9 mL) and tetrahydrofuran (1.8 mL). The reaction mixture was stirred at room temperature overnight, and it was then partitioned between water (100 mL) and ether (100 mL). The aqueous layer was acidified with 1 M HCl to pH<3 and the resulting mixture was extracted with chloroform (100 mL). The chloroform extract was washed with brine (100 mL), dried (magnesium sulfate), filtered, and evaporated to give (4S,7R)-4-(1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid (168 mg, 77%) as a white solid.

Workup

  1. customit was then partitioned between water (100 mL) and ether (100 mL)
  2. extractionthe resulting mixture was extracted with chloroform (100 mL)
  3. extractionThe chloroform extract
  4. washwas washed with brine (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3957558e80744a08bf700ad0ea5ecba1
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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