2,6-Lutidine → Benzyl (2S)-cyclohexyl{[(trifluoromethyl)sulfonyl]oxy}ethanoate

HRID 1860507Notes

Reaction equation

HRID 1860507 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C@@H:17]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].N1C(C)=CC=CC=1C>C(Cl)Cl>[CH:28]1([C@H:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 54322505Benzyl (s)-hexahydromandelate

Product 1

HCID 86758873Benzyl (2S)-cyclohexyl{[(trifluoromethyl)sulfonyl]oxy}ethanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoromethanesulfonic anhydride (12.7 g, 45.2 mmol) in 40 mL CH2Cl2 was cooled in an ice bath. A solution of 2-(S)-hydroxy-2-(cyclohexyl)acetic acid, benzyl ester (10.7 g, 43 mmol, from Step A) and 2,6-lutidine (4.6 g, 43 mmol) in 40 mL CH2Cl2 was added dropwise over 25 min and the mixture was stirred for an additional 20 min. The mixture was washed with water and sat'd NaCl then the organic layer was dried over sodium sulfate and concentrated. Flash chromatography (150 g silica, 0→15% EtOAc/hexanes) gave the desired product. 1H NMR (500 MHz, CDCl3) δ1.09-1.33 (m, 5H), 1.66-1.73 (m, 2H), 1.75-1.83 (m, 2H), 2.01-2.08 (m, 1H), 4.98 (d, 1H), 5.27 (d, 1H), 5.29 (d, 1H), 7.35-7.4 (m, 5H).

Workup

  1. washThe mixture was washed with water
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d81bdf1ff2bb4547906534a607ebc3bb
Source dataset
uspto-grants-2003_03
Patent number
US06531484B2

Reaction notes

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