Hydrochloric Acid → HCID 67270826, compound

HRID 600856Notes

Reaction equation

HRID 600856 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][N:14]([CH2:25][CH3:26])[C:15]2[CH:20]=[CH:19][N: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>O1CCOCC1>[NH2:8][C@@H:12]([CH2:13][N:14]([CH2:25][CH3:26])[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67271115HCID 67271115, compound

Product 1

HCID 67270826HCID 67270826, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(S)-4-{[Ethyl-(2-trifluoromethyl-pyrimidin-4-yl)-amino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.339 g, 0.84 mmol) was dissolved in dioxane (6 ml), aqueous hydrochloric acid (4N, 6 ml) was added and the mixture was stirred at 60° C. for 3 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=95:5) yielded a light yellow liquid, (0.19 g, 86%); MS (ISP): 265.3 ((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=95:5) yielded a light yellow liquid, (0.19 g, 86%)

Sources & evidence

ORD record
ord-3d922d06f803461cb042d57fa802dac2
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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