Potassium Hydroxide → erythro-N-Boc-D-phenylalanine epoxide

HRID 424978

Reaction equation

HRID 424978 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:9]([OH:12])[CH2:10]Cl)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([C@@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 60170213HCID 60170213, compound

Product 1

HCID 11357515erythro-N-Boc-D-phenylalanine epoxideYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (R,R)-1-benzyl-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester (4.45 g, 15 mmol) in ethanol (125 mL) at 0° C. is added KOH (0.5M in ethanol, 36 ml, 18 mmol). After stirring for 20 min, the mixture is concentrated under reduced pressure and the residue is dissolved in ethyl acetate, washed with saturated ammonium chloride (aq), water and then brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting white solid is purified using General Purification Procedure E to afford the title compound as a white solid (2.7 g, 10.4 mmol).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with saturated ammonium chloride (aq), water
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting white solid is purified
  7. customGeneral Purification Procedure E

Sources & evidence

ORD record
ord-2f53e88e4ec4460b9f8801f6c321376e
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Linked notes

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