HCID 86622950, compound → HCID 86622953, compound

HRID 2428162Notes

Reaction equation

HRID 2428162 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH2:20][OH:21])[CH:14]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2]>CC#N.O=[Mn]=O>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH:20]=[O:21])[CH:14]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86622950HCID 86622950, compound

Product 1

HCID 86622953HCID 86622953, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (3.89 g, 40.2 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (2.71 g, 18.2 mmol) in CH3CN (85 mL) at rt. The mixture was stirred at rt for 4 h, and MnO2 (2.71 g, 18.2 mmol) was added again. The mixture was stirred overnight. The mixture was filtered over Celite, and the precipitate was washed with CH3CN and CH2Cl2. The filtrate was evaporated under reduced pressure to yield the crude title compound (2.80 g, quantitative yield) that was used further without purification. LC-MS: tR=1.03 min; ES+: not visible.

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationThe mixture was filtered over Celite
  3. washthe precipitate was washed with CH3CN and CH2Cl2
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-741370cc249b4e92b9a681655c5bbb68
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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