Methanesulfonyl chloride → HCID 69422676, compound

HRID 459204Notes

Reaction equation

HRID 459204 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:23][CH3:24])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][C:8]=1[O:21][CH3:22])O.S(Cl)(C)(=O)=O>CN(C1C=CN=CC=1)C.ClCCl.CCOCC.CO>[CH3:1][O:2][C:3](=[O:25])[CH:4]([O:23][CH3:24])[CH2:5][C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:15])[CH3:16])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

7

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69425307HCID 69425307, compound

Product 1

HCID 69422676HCID 69422676, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-[4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-phenyl]-3-hydroxy-2-methoxy-propionic acid methyl ester (1 eq), Mesylchloride (1 eq) triethylamine (4 eq) and a catalytic amount of DMAP (0.1 eq) in dichloromethane was stirred at room temperature over night. The reaction mixture was diluted with ether and washed with HCl 1N. Dried and concentrated in vacuo to give a residue which was chromatographed in silica gel to yield a compound which was dissolved in methanol was treated with Mg (20 eq) and stirred until gas evolution was observed. Cooled to 0° C. and stirred for 4 hours. The solvent was removed and the residue reconstituted in ether washed with HCl 1N and brine and concentrated to give the title product.

Workup

  1. washwashed with HCl 1N
  2. customDried
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas chromatographed in silica gel
  6. customto yield a compound which
  7. stirringstirred for 4 hours
  8. customThe solvent was removed
  9. washwashed with HCl 1N and brine
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-74a56e641428445facdbcd15ee00992c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…