Acetone → HCID 53833991, compound

HRID 2226588Notes

Reaction equation

HRID 2226588 reaction equation
[CH3:1][C:2](=O)[CH3:3].Cl.[CH2:6]([O:9][C:10](=[O:15])[C@@H:11]([OH:14])[CH2:12][NH2:13])[CH:7]=[CH2:8].C(N(CC)CC)C.[BH4-].[Na+]>C(O)C.ClCCl.O>[CH2:6]([O:9][C:10](=[O:15])[C@@H:11]([OH:14])[CH2:12][NH:13][CH:2]([CH3:3])[CH3:1])[CH:7]=[CH2:8]

Participants

8

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 88136262HCID 88136262, compound

Product 1

HCID 53833991HCID 53833991, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Propanone (0.22 g, 3.7 mmol) was added to a solution of (S)-3-amino-2-hydroxypropanoic acid 2-propenyl ester hydrochloride (0.45 g, 2.5 mmol) and triethylamine (0.25 g, 2.5 mmol) in ethanol (2.5 ml). After 2 h the solution was cooled to 0° and sodium borohydride (0.15 g, 3.9 mmol) was added. After 20 min, water (0.4 ml) and dichloromethane were added. The mixture was filtered and the filtrate evaporated. The residue was dissolved in ether/water, the organic layer dried (MgSO4) and the solvent evaporated to give the sub-title ester (0.15 g).

Workup

  1. temperatureAfter 2 h the solution was cooled to 0°
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in ether/water
  5. dry with materialthe organic layer dried (MgSO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-41369a8e26d047fab0db4e47ea52f62d
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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