Sodium Hydroxide → HCID 57187001, compound

HRID 2299667Notes

Reaction equation

HRID 2299667 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][CH2:12][CH:11]([N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][C@H:17]([OH:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][C:9]=2[CH:34]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[C:30]([O:29][C:27]([N:15]([CH:11]1[CH2:10][C:9]2[CH:34]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=2[CH2:14][CH2:13][CH2:12]1)[CH2:16][C@H:17]([OH:26])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57047404HCID 57047404, compound

Product 1

HCID 57187001HCID 57187001, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-[N-tert-butoxycarbonyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid methyl ester (4.5 g) in methanol (45 ml) and tetrahydrofuran (15 ml) was added 1N sodium hydroxide aqueous solution. After stirring at room temperature for 6 hours, the reaction mixture was concentrated under reduced pressure, neutralized with 1N hydrochloric acid solution under ice-cooling. The product was extracted with ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford 8-[N-tert-butoxycarbonyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid (4.48 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. temperaturecooling
  3. extractionThe product was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb1562d4aa5648409c42e17cd17fa648
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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