Trifluoromethanesulfonic acid → 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

HRID 1872235Notes

Reaction equation

HRID 1872235 reaction equation
C([O:5][C:6]([CH:8]1[CH:14]([CH2:15][OH:16])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])(C)(C)C.ClC(Cl)(Cl)C(=N)O[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.FC(F)(F)S(O)(=O)=O>C1CCCCC1.ClCCl>[CH2:32]([O:16][CH2:15][CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:8]1[C:6]([OH:5])=[O:7])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 541061343-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Product 1

HCID 186896293-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-Hydroxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (110 mg, 0.275 mmoL) in 3.9 mL cyclohexane and 1.95 mL of dichloromethane was added benzyl trichloracetimidate (0.1 mL, 0.55 mmoL). The solution was cooled to 0° C. and trifluoromethane sulfonic acid (0.008 mL, 0.091 mmoL) was added in. After 2.5 hours the reaction was filtered and the cake was washed with a 2:1 solution of cyclohexane and dichloromethane, the solvent was evaporated under reduced pressure and the residue was taken up in ethyl acetate. The solution was washed sequentially with dilute sodium bicarbonate and brine. The organic layer was dried over anhyrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The residue was purified by column chromatography (silica: 30% ethyl acetate in hexanes to 5% methanol in dichloromethane) to yield 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid; MS: (M+H)+ =434, (M-H)- =432.

Workup

  1. filtrationAfter 2.5 hours the reaction was filtered
  2. washthe cake was washed with a 2:1 solution of cyclohexane and dichloromethane
  3. customthe solvent was evaporated under reduced pressure
  4. washThe solution was washed sequentially with dilute sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over anhyrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silica: 30% ethyl acetate in hexanes to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d07d26c707314199886eeb817bcedafa
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

Loading…