Trifluoroacetic acid → HCID 71718352, compound

HRID 1520244Notes

Reaction equation

HRID 1520244 reaction equation
C(OC(=O)[NH:7][C:8]1[O:9][CH2:10][C:11]([F:36])([F:35])[C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]([C:24]3[CH:29]=[N:28][C:27]([O:30][CH2:31][C:32]#[CH:33])=[CH:26][N:25]=3)=[O:23])[CH:18]=[CH:17][C:16]=2[F:34])([CH3:14])[N:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[O:9][CH2:10][C:11]([F:35])([F:36])[C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:22]([C:24]3[CH:29]=[N:28][C:27]([O:30][CH2:31][C:32]#[CH:33])=[CH:26][N:25]=3)=[O:23])[CH:18]=[CH:17][C:16]=2[F:34])([CH3:14])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86716458HCID 86716458, compound

Product 1

HCID 71718352HCID 71718352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

((R)-5,5-Difluoro-4-{2-fluoro-5-[(5-prop-2-ynyloxy-pyrazine-2-carbonyl)-amino]-phenyl}-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-carbamic acid tert-butyl ester (350 mg, 674 μmol) was combined with DCM (5.2 ml) to give a light yellow solution. The solution was cooled to 0° C. and TFA (768 mg, 519 μl, 6.74 mmol) was added. After stirring 30 min at 0° C. the ice bath was removed and the reaction was allowed to warm up and was stirred at RT for 6 h. The pH of the reaction mixture was adjusted to 8 by dropwise addition of sat. aq. NaHCO3 and the product was extracted with DCM. The organic layers were dried over Na2SO4 and concentrated under vacuum. A colorless foam was obtained that was purified by flash chromatography (SiO2, 10 g, 0 to 80% EtOAc in heptane). Colorless foam (230 mg, 81%). MS (ISP): m/z=420.1 [M+H]+.

Workup

  1. customto give a light yellow solution
  2. customwas removed
  3. temperatureto warm up
  4. additionThe pH of the reaction mixture was adjusted to 8 by dropwise addition of sat. aq. NaHCO3
  5. extractionthe product was extracted with DCM
  6. dry with materialThe organic layers were dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customA colorless foam was obtained
  9. customthat was purified by flash chromatography (SiO2, 10 g, 0 to 80% EtOAc in heptane)

Sources & evidence

ORD record
ord-bbe833d8b57b421a9eb976c9b75e9588
Source dataset
uspto-grants-2015_07
Patent number
US09073909B2

Reaction notes

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