Trifluoroacetic acid → HCID 117662140, compound

HRID 1484413Notes

Reaction equation

HRID 1484413 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:23])(=[N:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[O:15])=[CH:10][CH:9]=2)[O:6]C(C)(C)[N:4]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:4][C@H:3]([CH2:2][F:1])[C@@H:7]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:23])(=[N:16][C:17](=[O:22])[C:18]([F:20])([F:21])[F:19])=[O:15])=[CH:12][CH:13]=1)[OH:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117655239HCID 117655239, compound

Product 1

HCID 117662140HCID 117662140, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl)phenyl)oxazolidine-3-carboxylate (500 mg, 1.168 mmol) in DCM (20 mL) is added Trifluoroacetic acid (2.0 mL). Reaction mixture is allowed to stir at room temperature for 2 h. Excess of Trifluoroacetic acid and DCM is evaporated in vacuo, stripped with toluene followed by washing with n-pentane and diethyl ether to afford crude title compound (426 mg, TFA salt) as faint yellow sticky mass which is used as such for next step.

Workup

  1. customReaction mixture
  2. customExcess of Trifluoroacetic acid and DCM is evaporated in vacuo
  3. washby washing with n-pentane and diethyl ether

Sources & evidence

ORD record
ord-0787fbf48f1d46f8baded5bae255057f
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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