Trifluoroacetic acid → HCID 16225554, compound

HRID 2355205Notes

Reaction equation

HRID 2355205 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH:10]1[CH2:19][C:18]([OH:21])([CH3:20])[C:17]2[C:12](=[CH:13][C:14]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:15][CH:16]=2)[O:11]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.FC(F)(F)C([O-])=O>C(Cl)Cl>[C:25]1([S:22]([C:14]2[CH:13]=[C:12]3[C:17]([C:18]([CH3:20])([OH:21])[CH2:19][CH:10]([CH2:9][NH:7][CH3:6])[O:11]3)=[CH:16][CH:15]=2)(=[O:23])=[O:24])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 84468TrifluoroacetateHCID 58869160HCID 58869160, compound

Product 1

HCID 16225554HCID 16225554, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-benzenesulfonyl-4-hydroxy-4-methyl-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (212 mg, 0.474 mmol) in DCM (10 mL) was added TFA (1 mL). The reaction was stirred for 3 hours at room temperature, then concentrated in vacuo. The residue was purified via flash chromatography (DCM/MeOH/TEA) to give 7-benzenesulfonyl-4-methyl-2-methylaminomethyl-chroman-4-ol (63 mg, 38% yield) as a trifluoroacetate salt: Mp 163.9-165.3° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via flash chromatography (DCM/MeOH/TEA)

Sources & evidence

ORD record
ord-3794011512634d7aafc1fb9d5b20c213
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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