Trifluoromethanesulfonic acid → HCID 59485955, compound

HRID 1972202Notes

Reaction equation

HRID 1972202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[C@H:11]([CH2:23][OH:24])[O:10][C:9]2=[O:25])=[CH:4][CH:3]=1.[CH2:26](OC(=N)C(Cl)(Cl)Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.FC(F)(F)S(O)(=O)=O>ClCCl>[CH2:26]([O:24][CH2:23][C@@H:11]1[O:10][C:9](=[O:25])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C@H:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 68701678HCID 68701678, compound

Product 1

HCID 59485955HCID 59485955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4S,5R)-3-(4-chlorophenyl)-4-(3-(trifluoromethyl)phenyl)-5-(hydroxymethyl)-oxazolidin-2-one (0.08 mmol), prepared according to the method described for Example 64, in dichloromethane (1 mL) was treated with benzyltrichloroacetimidate (0.09 mmol) and catalytic trifluoromethane sulfonic acid. The reaction was stirred overnight, and was then purified on silica gel (10-30% ethyl acetate/hexanes) to give the title compound. 1H NMR (acetone-d6) δ (ppm) 7.82 (s, 1H), 7.74 (d, J=7.6 Hz, 1H) 7.68 (d, J=7.7 Hz, 1H), 7.65-7.61 (m, 1H), 7.54-7.52 (m, 2H), 7.37-7.28 (m, 6H), 5.72 (d, J=5.3 Hz, 1H), 4.71-4.62 (m, 3H), 3.95 (d, J=3.8 Hz, 2H); HPLC-MS calculated C24H19ClF3NO3 (M+H+): 462.1, found: 461.9.

Workup

  1. customwas then purified on silica gel (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c9480e516b6d4c92b5abe47146f0ec5a
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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