Pyridine → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate

HRID 1842966Notes

Reaction equation

HRID 1842966 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9][OH:10])=[C:4]([F:14])[CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>CC(C)=O>[OH:12][CH2:11][C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][C:4]=1[F:14])([CH3:13])[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721622-(4-Amino-2-fluorophenyl)-2-methylpropane-1,3-diol

Product 1

HCID 86672163Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamateYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(4-amino-2-fluorophenyl)-2-methylpropane-1,3-diol (1.5 g, 7.53 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (1.2 g, 15.18 mmol, 2.0 eq) and phenyl chloroformate (1.3 g, 8.28 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The acetone was evaporated, and the resulting residue was diluted with EtOAc (50 mL), washed with water (100 mL), brine (20 mL) and the solvent evaporated. The crude product was purified by silica CC using EtOAc/PE (3:2) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate (1.7 g, 71%) as a white solid (TLC system: EtOAc/PE (7:3), Rf: 0.55).

Workup

  1. customThe acetone was evaporated
  2. additionthe resulting residue was diluted with EtOAc (50 mL)
  3. washwashed with water (100 mL), brine (20 mL)
  4. customthe solvent evaporated
  5. customThe crude product was purified by silica CC

Sources & evidence

ORD record
ord-955180924293465d9de3ba230f61d19d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…