Potassium Hydroxide → HCID 59786775, compound

HRID 424982Notes

Reaction equation

HRID 424982 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[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:22])[NH:7][C@@H:8]([C@@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66703639HCID 66703639, compound

Product 1

HCID 59786775HCID 59786775, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of (R,R)-1-(2,5-difluorophenylmethyl)-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester (2.2 g, 6.6 mmol) in ethanol (100 mL) at 0° C. is added a 0.5M solution of KOH in ethanol (15.7 mL, 7.9 mmol, 1.2 eq) and is stirred for 90 min. The reaction mixture is concentrated under reduced pressure and the residue is redissolved in ethyl acetate. The solution is washed sequentially with saturated ammonium chloride (aq), water and brine, then dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as a white solid (1.86 g, 6.2 mmol).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe residue is redissolved in ethyl acetate
  3. washThe solution is washed sequentially with saturated ammonium chloride (aq), water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7d6c49cc3ed47c09a07fe532e5204ce
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Reaction notes

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