HCID 86655664, compound → HCID 86655665, compound

HRID 2047465Notes

Reaction equation

HRID 2047465 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([N:13]([CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>C(O)(=O)C.O.C1COCC1>[F:1][C:2]([F:31])([F:32])[C:3]1[CH:4]=[C:5]([N:13]([CH2:21][CH2:22][OH:23])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

5

Reactant 1

HCID 86655664HCID 86655664, compound

Product 1

HCID 86655665HCID 86655665, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of the compound (0.50 g) obtained in step 3 in acetic acid (6 mL), water (2 mL) and THF (2 mL) was stirred at 50° C. for 14 hr, poured into water, and extracted with diethyl ether. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 10→33% ethyl acetate/hexane) to give tert-butyl [3,5-bis(trifluoromethyl)phenyl](2-hydroxyethyl)carbamate (0.34 g, 87%) as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 10→33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cc7528f0d9de4fc88738bc58225210b1
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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