Ethyl Acetate → Benzyl ((2R)-1-hydroxypropan-2-yl)carbamate

HRID 1901682Notes

Reaction equation

HRID 1901682 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@H:13]([CH2:15][OH:16])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]([NH:12][C@H:13]([CH3:14])[CH2:15][OH:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 80308(R)-(-)-2-Amino-1-propanol

Product 1

HCID 6951254Benzyl ((2R)-1-hydroxypropan-2-yl)carbamateYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.42 g of benzyloxycarbonyl chloride were added dropwise to a mixture of 5.00 g of D-alaninol, 18.49 g of potassium carbonate, 15 ml of ethyl acetate and 15 ml of water, and the mixture was stirred at room temperature for 1.5 hours. At the end of this time, the ethyl acetate layer was separated, and the aqueous layer was extracted with ethyl acetate. The ethyl acetate layer and the extract were combined, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The crude crystals which precipitated were collected by filtration and washed with hexane, to give 13.68 g of the title compound, melting at 78° C. to 80° C.

Workup

  1. customAt the end of this time, the ethyl acetate layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe crude crystals which precipitated
  6. filtrationwere collected by filtration
  7. washwashed with hexane

Sources & evidence

ORD record
ord-9b3adef179e94f43ae9e04bf017ebfae
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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