Trifluoroacetic acid → HCID 86695483, compound

HRID 525597Notes

Reaction equation

HRID 525597 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([CH2:27][NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C1(C)C=CC=CC=1>[NH2:8][C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH:28][S:29]([CH3:32])(=[O:30])=[O:31])=[N:23][CH:22]=2)=[CH:17][CH:16]=1)[OH:10]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86695484HCID 86695484, compound

Product 1

HCID 86695483HCID 86695483, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

(4S,5R)-tert-butyl4-(fluoromethyl)-2,2-dimethyl-5-(4-(6-(methylsulfonamido-methyl)pyridin-3-yl)phenyl)oxazolidine-3-carboxylate (1800 mg, 3.64 mmol) is dissolved in dichloromethane (20 mL), and treated with trifluoroacetic acid (5.4 mL), for 4 h at room temperature. The reaction mixture is diluted with toluene (30 mL) and concentrated to a syrup. Obtained crude compound is basified with aqueous sodium bicarbonate, extracted with ethyl acetate. Extracts are dried over Na2SO4, filtered, and concentrated to give the title compound (1110 mg): m/z (Cl) M+H 354.

Workup

  1. concentrationconcentrated to a syrup
  2. customObtained crude compound
  3. extractionextracted with ethyl acetate
  4. dry with materialExtracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1763b9f03a814ae1b9f210b625a44f16
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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