Pyridine → HCID 86589055, compound

HRID 2414382Notes

Reaction equation

HRID 2414382 reaction equation
N1C=CC=CC=1.[S:7]([O:14]S(C(F)(F)F)(=O)=O)([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8].O[C@H:23]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=1)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[F:11][C:10]([F:13])([F:12])[S:7]([O:14][C@H:23]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=1)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86589054HCID 86589054, compound

Product 1

HCID 86589055HCID 86589055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of pyridine (0.78 mL, 9.7 mmol) in CH2Cl2 (50 mL) at −10° C. is added triflic anhydride (1.68 mL, 10.0 mmol) over 15 min. A solution of benzyl (R)-2-hydroxy-3-(3-methylphenyl)-propionate (1.5 g, 5.55 mmol) in CH2Cl2 (15 mL) is then added dropwise over 30 min., and the mixture is warmed to room temp. over 1 h. The solution is diluted with CH2Cl2 (100 mL), washed with water (2×100 mL) and brine (100 mL), dried (MgSO4), and evaporated to yield benzyl (R)-2-trifluoromethanesulfonyloxy-3-(3-methylphenyl)-propionate as a yellowish oil.

Workup

  1. temperaturethe mixture is warmed to room temp. over 1 h
  2. washwashed with water (2×100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9041c8e56f6e4eab9913fdd64b3356a6
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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