Sodium Hydroxide → HCID 69592271, compound

HRID 2213692Notes

Reaction equation

HRID 2213692 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:15]([NH:16][C:17]([C:19]2[S:20][C:21]([S:24]([N:27]3[CH:31]=[CH:30][CH:29]=[CH:28]3)(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[O:18])[C@@H:14]2[CH2:32][C@H:11]1[CH2:12][CH2:13]2.[OH-].[Na+]>CO.O1CCCC1.O>[N:27]1([S:24]([C:21]2[S:20][C:19]([C:17]([NH:16][C@H:15]3[C@@H:14]4[CH2:32][C@@H:11]([CH2:12][CH2:13]4)[C@@H:10]3[CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[O:18])=[CH:23][CH:22]=2)(=[O:26])=[O:25])[CH:31]=[CH:30][CH:29]=[CH:28]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 69592241HCID 69592241, compound

Product 1

HCID 69592271HCID 69592271, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 350 mg (0.713 mmol) of (5Z)-7-{(1R,2S,3S,4S)-3-[5-(pyrrol-1-ylsulfonyl)thiophen-2-ylcarbonylamino]-bicyclo[2.2.1]hept-2-yl}-5-heptenoic acid methyl ester (I-1a) in 1 ml of methanol and 0.5 ml of tetrahydrofuran was added under ice-cooling 0.5 ml (2.0 mmol) of 4N sodium hydroxide. The mixture was warmed to room temperature and stirred at 25° C. for 2 h. The reaction mixture was diluted with water and washed with ether. The aqueous layer was acidified with 0.5 ml of 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane (3:4) to give 234 mg of (5Z)-7-{(1R,2S,3S,4S)-3-[5-(pyrrol-1-ylsulfonyl)-thiophen-2-ylcarbonylamino]-bicyclo[2.2.1]hept-2-yl}-5-heptenoic acid (I-1b) as needles.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane (3:4)

Sources & evidence

ORD record
ord-611f7571cf2844e888430c25c5d477be
Source dataset
uspto-grants-2006_09
Patent number
US07105564B1

Reaction notes

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