Trifluoroacetic acid → Trifluoroacetic acid

HRID 1500300Notes

Reaction equation

HRID 1500300 reaction equation
[O:1]=[S:2]1(=[O:34])[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([C@H:18]4[O:22]C(C)(C)[N:20](C(OC(C)(C)C)=O)[C@@H:19]4[CH2:32][F:33])=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3]1.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(Cl)Cl>[C:37]([OH:39])([C:36]([F:41])([F:40])[F:35])=[O:38].[NH2:20][C@H:19]([CH2:32][F:33])[C@@H:18]([C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]([C:4]3[CH2:5][S:2](=[O:1])(=[O:34])[CH:3]=3)=[N:11][CH:10]=2)=[CH:17][CH:16]=1)[OH:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713187(4S,5R)-tert-butyl 5-(4-(6-(1,1-dioxido-2H-thiet-3-yl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 867131883-(5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)phenyl)pyridin-2-yl)-2H-thiete 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product of step 4, Example 18 (0.15 g, 0.233 mmol, 1 eq) in methylene chloride (5 mL) is added trifluoroacetic acid (0.4 mL) at 0° C. Resulting reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is concentrated in vacuo and stripped with methylene chloride (3×10 mL) to afford crude TFA salt of title compound (0.185 g), which is used as such in next step. LCMS (m/z): [M+H] 349.1.

Workup

  1. customResulting
  2. customreaction mixture
  3. concentrationThe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-f55c4650e501411ab4df77171d665f03
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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