Methanesulfonyl chloride → HCID 86592574, compound

HRID 1985390Notes

Reaction equation

HRID 1985390 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C@@H:15]([OH:36])[C@H:16]([O:32][CH:33]([CH3:35])[CH3:34])[C:17]([N:19]2[C@@H:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:22][O:21][C:20]2=[O:31])=[O:18])[CH:10]=1)(C)(C)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>N1C=CC=CC=1.C(OCC)(=O)C>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C@@H:15]([O:36][S:39]([CH3:38])(=[O:41])=[O:40])[C@H:16]([O:32][CH:33]([CH3:35])[CH3:34])[C:17]([N:19]2[C@@H:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:22][O:21][C:20]2=[O:31])=[O:18])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57719758HCID 57719758, compound

Product 1

HCID 86592574HCID 86592574, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

19.2 g of {3-[3-(4 (S)-Benzyl-2-oxooxazolidin-3-yl)-1-(R)-hydroxy-2(S)-isopropoxy-3-oxopropyl]benzyl}-carbamic acid t-butyl ester was dissolved in 100 ml of pyridine, and 4.35 ml of methanesulfonyl chloride was added dropwise under ice-cooling. After stirring was continued for 2 hours under ice-cooling and for 3 hours at room temperature, the reaction solution was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated, to give methanesulfonic acid 1 (R)-(3-aminomethylphenyl)-3-(4 (S)-benzyl-2-oxooxazolidin-3-yl)-2(S)-isopropoxy-3-oxopropyl ester. This product was dissolved in 500 ml of ethanol, and 10 g of 10% palladium carbon and 5 g of potassium acetate were added, and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The reaction solution was filtered and the filtrate was concentrated. The residue was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 15.3 g of the title compound as a white solid in the 2:1→3:2 hexane-ethyl acetate fraction.

Workup

  1. temperaturecooling
  2. washwashed successively with 1N hydrochloric acid and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-34c70de6cdf544358b9a854e2cb27efd
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

Loading…