Sodium Hydroxide → HCID 57815115, compound

HRID 1160468Notes

Reaction equation

HRID 1160468 reaction equation
C[O:2][C:3](=[O:40])[C@H:4]([OH:39])[C@@H:5]([NH:13][C:14](=[O:38])[C:15]1[CH:20]=[C:19]([C:21]([NH:23][C@@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])=[O:22])[CH:18]=[C:17]([N:32]([CH3:37])[S:33]([CH3:36])(=[O:35])=[O:34])[CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[OH:39][C@H:4]([C@@H:5]([NH:13][C:14](=[O:38])[C:15]1[CH:20]=[C:19]([C:21]([NH:23][C@@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])=[O:22])[CH:18]=[C:17]([N:32]([CH3:37])[S:33]([CH3:36])(=[O:35])=[O:34])[CH:16]=1)[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:3]([OH:40])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57815131HCID 57815131, compound

Product 1

HCID 57815115HCID 57815115, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 10 ml solution of (2R,3S)-2-hydroxy-3-{[3-[methyl(methylsulfonyl)amino]-5-({[(1R)-1-phenylethyl]amino}carbonyl)-benzoyl]amino}-4-phenylbutanoic acid methylester 775 mg (1.37 mmol) in methanol was added 1N aqueous sodium hydroxide solution 1.64 ml and the mixture was stirred at room temperature for 5 hours. After distilling methanol off, the mixture was washed with ether. The mixture was adjusted with 1N hydrochloric acid to pH 3 under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried on magnesium sulfate, filtered and concentrated to give the title compound 730 mg (1.32 mmol) (yield 96%).

Workup

  1. distillationAfter distilling methanol off, the mixture
  2. washwas washed with ether
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5ca3ceaf77384c908bde36d0bfe2303c
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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