Hydrochloric Acid → HCID 68715428, compound

HRID 1911545Notes

Reaction equation

HRID 1911545 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>C(O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[N:16]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68714853HCID 68714853, compound

Product 1

HCID 68715428HCID 68715428, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

(S)-2,2-Dimethyl-4-[2-(6-trifluoromethyl-pyridin-2-yl)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester (0.522 g, 1.39 mmol) was dissolved in ethanol (2.5 ml), hydrochloric acid in ethanol (5N, 2.5 ml) was added and the mixture was stirred at 60° C. for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane. A solution of ammonia in methanol (2N, 2 ml) was added and the mixture was evaporated over Isolute® Flash-NH2 silicagel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=90:10) yielded a colourless liquid, (0.237 g, 73%); MS (ISP): 235.1 ((M+H)+.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. additionA solution of ammonia in methanol (2N, 2 ml) was added
  4. customthe mixture was evaporated over Isolute® Flash-NH2 silicagel
  5. customChromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=90:10) yielded a colourless liquid, (0.237 g, 73%)

Sources & evidence

ORD record
ord-fd8234623d784e30909a9e7374c2776c
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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