HCID 54085496, compound → HCID 15498792, compound

HRID 1740418Notes

Reaction equation

HRID 1740418 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C>C(O)=O>[CH2:15]([O:14][CH2:13][C@@H:9]([CH:10]([CH3:12])[CH3:11])[NH2:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 54085496HCID 54085496, compound

Product 1

HCID 15498792HCID 15498792, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of N-tert-butoxycarbonyl-O-benzyl-D-valinol (9.95 g, 34 mmol) in formic acid (50 mL) is stirred for 4 hours at room temperature. After removal of the formic acid under vacuum, the sticky residue is dissolved in water (100 mL), neutralized with a saturated solution of sodium bicarbonate (100 mL) and the organic material is extracted twice with ethyl acetate (2×200 mL). The organic phases are washed until neutral with water (2×200 mL) and the combined organic layers are dried over anhydrous sodium sulfate. Filtration and concentration under vacuum provides O-benzyl-D-valinol as a slightly yellowish oil (5.20 g, 79%).

Workup

  1. customAfter removal of the formic acid under vacuum
  2. dissolutionthe sticky residue is dissolved in water (100 mL)
  3. extractionthe organic material is extracted twice with ethyl acetate (2×200 mL)
  4. washThe organic phases are washed until neutral with water (2×200 mL)
  5. dry with materialthe combined organic layers are dried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration under vacuum

Sources & evidence

ORD record
ord-bc12231c783e428f9dc06385cd930578
Source dataset
uspto-grants-1999_10
Patent number
US05969132

Reaction notes

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