Trifluoromethanesulfonic anhydride → HCID 54052594, compound

HRID 987057Notes

Reaction equation

HRID 987057 reaction equation
[CH3:1][CH:2]1[CH:11]=[C:10]2[CH:5]([CH:6]([CH2:13][CH2:14][CH:15]([OH:22])[CH2:16][CH:17]([OH:21])[CH2:18][CH2:19]O)[CH:7]([CH3:12])[CH:8]=[CH:9]2)[CH:4]([O:23][C:24](=[O:29])[CH:25]([CH3:28])[CH2:26][CH3:27])[CH2:3]1.CCN(C(C)C)C(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(Cl)Cl>[OH:21][CH:17]1[CH2:18][CH2:19][O:22][CH:15]([CH2:14][CH2:13][CH:6]2[CH:5]3[C:10](=[CH:11][CH:2]([CH3:1])[CH2:3][CH:4]3[O:23][C:24](=[O:29])[CH:25]([CH3:28])[CH2:26][CH3:27])[CH:9]=[CH:8][CH:7]2[CH3:12])[CH2:16]1

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 20678451HCID 20678451, compound

Product 1

HCID 54052594HCID 54052594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−77° C.) solution of 73 mg (0.18 mmol) of 2-methyl-butyric acid 3,7-dimethyl-8-(3,5,7-trihydroxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml of methylene chloride is added 0.9 g (7 mmol) Hunig's base and 0.08 ml (0.5 mmol) triflic anhydride. After 30 minutes the reaction is quenched with saturated aqueous sodium bicarbonate. The phases are separated and the water phase is extracted twice with ethyl acetate. The organic phases are combined, washed with brine and dried over sodium sulfate. The solvent is evaporated and the crude product is purified by silica gel chromatography (diethyl ether/hexane 1/4) to afford the desired product as a colorless oil.

Workup

  1. customAfter 30 minutes the reaction is quenched with saturated aqueous sodium bicarbonate
  2. customThe phases are separated
  3. extractionthe water phase is extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated
  7. customthe crude product is purified by silica gel chromatography (diethyl ether/hexane 1/4)

Sources & evidence

ORD record
ord-30db6072d4bf45dcb20f58df83e5b3d3
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

Loading…