Sodium Hydroxide → HCID 57815082, compound

HRID 1160461Notes

Reaction equation

HRID 1160461 reaction equation
C[O:2][C:3](=[O:46])[C@H:4]([O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[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>[CH3:37][N:32]([S:33]([CH3:36])(=[O:35])=[O:34])[C:17]1[CH:16]=[C:15]([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]=1)[C:14]([NH:13][C@@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C@@H:4]([O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[C:3]([OH:46])=[O:2])=[O:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57815104HCID 57815104, compound

Product 1

HCID 57815082HCID 57815082, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The (2R,3S)-3-{[3-[methyl(methylsulfonyl)amino]-5-({[(1R)-1-phenylethyl]amino}carbonyl)benzoyl]amino}-4-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)butanoic acid methylester obtained in Reference Example 26 1.79 g (2.75 mmol) was dissolved in methanol 6 mL and thereto was added 5N aqueous sodium hydroxide solution 1.10 mL under ice-cooling and the mixture was stirred at room temperature for 6 hours. After distillating methanol off, the mixture was washed with ether. The aqueous layer was adjusted with diluted hydrochloric acid to pH 3 under ice-cooling and extracted with chloroform. The organic layer was washed with an aqueous saturated sodium chloride solution and dried on magnesium sulfate, filtered and concentrated to give 1.74 g (2.73 mmol) of the title compound (yield: 99%).

Workup

  1. temperaturecooling
  2. washwas washed with ether
  3. temperaturecooling
  4. extractionextracted with chloroform
  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-1ca62e7ec9334e27b176b9f3e2c9be7f
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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