Trifluoroacetic acid → HCID 131733108, compound

HRID 1487485Notes

Reaction equation

HRID 1487485 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]([CH:27]([CH:29]([CH3:31])[CH3:30])[NH2:28])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[O:10]C1(C)C)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[OH:38][C:36]([C:35]([F:40])([F:39])[F:34])=[O:37].[NH2:8][C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[N:23][C:24]([CH:27]([CH:29]([CH3:31])[CH3:30])[NH2:28])=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[OH:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89790682HCID 89790682, compound

Product 1

HCID 131733108HCID 131733108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4R,5R)-4-Fluoromethyl-5-{4-[6-(isopropyl amino-methyl)-pyridin-3-yl]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (100 mg, 0.218 mmol) in CH2Cl2 (0.17 mL) is added trifluoroacetic acid (0.4 mL) at 0° C. Reaction mixture is allowed to stir at room temperature for 2 hours. The volatiles are removed under reduced pressure and crude material is purified by column chromatography over basic alumina using 50% methanol in CH2Cl2 as eluent to afford title compound (70 mg, impure). LC-MS (m/z): [M+H]=318.2.

Workup

  1. customReaction mixture
  2. customThe volatiles are removed under reduced pressure and crude material
  3. customis purified by column chromatography over basic alumina using 50% methanol in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-d6e3ae41190143dabb687d4bbee7ecde
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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