Potassium Phosphate, Tribasic → HCID 86711701, compound

HRID 1855312Notes

Reaction equation

HRID 1855312 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:13]=1)=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[BH4-].[Na+]>C(O)C>[C:28]([Si:25]([CH3:27])([CH3:26])[O:24][C@H:18]([C:15]1[CH:14]=[CH:13][C:12]([N:7]2[C@@H:6]([CH2:4][OH:3])[CH2:10][CH2:9][C:8]2=[O:11])=[CH:17][CH:16]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 4311764Sodium borohydrideHCID 86711700HCID 86711700, compound

Product 1

HCID 86711701HCID 86711701, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a flask containing ethanol and (R)-1-{4-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester was added aqueous potassium phosphate bibasic followed by an aqueous solution of sodium borohydride, while maintaining the reaction at ambient temperature (˜23° C.). The mixture was stirred at ambient temperature until all of the ethyl ester was consumed before quenching with water, and then extracted with MTBE. The combined organic extracts were washed with brine and concentrated under reduced pressure to give crude product as an off-white solid. The crude product was re-crystallized with heptanes to give a pure product.

Workup

  1. temperaturewhile maintaining
  2. customthe reaction at ambient temperature (˜23° C.)
  3. customwas consumed
  4. custombefore quenching with water
  5. extractionextracted with MTBE
  6. washThe combined organic extracts were washed with brine
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product as an off-white solid
  9. customThe crude product was re-crystallized with heptanes
  10. customto give a pure product

Sources & evidence

ORD record
ord-b4a841b72ba24f54926e2c010ba0c729
Source dataset
uspto-grants-2015_02
Patent number
US08962863B2

Reaction notes

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