HCID 54085496, compound → HCID 15498792, compound

HRID 355546Notes

Reaction equation

HRID 355546 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) was stirred for 4 hours at room temperature. After removal of the formic acid in vacuo, the sticky residue was dissolved in water (100 ml), neutralized with a saturated solution of sodium bicarbonate (100 ml) and the organic material extracted twice with ethyl acetate (2×200 ml). The organic phases were washed until neutral with water (2×200 ml) and the combined organic layers were dried on sodium sulfate. Filtration and evaporation of the solvent in vacuo afforded the title amine as a slightly yellowish oil (5.20 g, 79%).

Workup

  1. customAfter removal of the formic acid in vacuo
  2. dissolutionthe sticky residue was dissolved in water (100 ml)
  3. extractionthe organic material extracted twice with ethyl acetate (2×200 ml)
  4. washThe organic phases were washed until neutral with water (2×200 ml)
  5. customthe combined organic layers were dried on sodium sulfate
  6. filtrationFiltration and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-bbe57e1e17a54d46b53bacb60b4b9b08
Source dataset
uspto-grants-1998_11
Patent number
US05831094

Reaction notes

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