Methanesulfonic acid 2-[3-benzyloxy-4-(5-benzyloxymethyl-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-5-fluorobenzyl]-4-methylphenyl ester → Methanesulfonic acid 2-[3-fluoro-5-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-4-methylphenyl ester

HRID 889247Notes

Reaction equation

HRID 889247 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:25]=[C:26]([F:45])[C:27]=1[N:28]1[CH2:32][C:31](=[O:33])[N:30](COCC2C=CC=CC=2)[S:29]1(=[O:44])=[O:43])[CH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[O:20][S:21]([CH3:24])(=[O:23])=[O:22])C1C=CC=CC=1>CCO.CCOC(C)=O.[Pd]>[F:45][C:26]1[CH:25]=[C:11]([CH:10]=[C:9]([OH:8])[C:27]=1[N:28]1[CH2:32][C:31](=[O:33])[NH:30][S:29]1(=[O:44])=[O:43])[CH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[O:20][S:21]([CH3:24])(=[O:22])=[O:23]

Participants

5

Reactant 1

HCID 86638981Methanesulfonic acid 2-[3-benzyloxy-4-(5-benzyloxymethyl-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-5-fluorobenzyl]-4-methylphenyl ester

Product 1

HCID 17747195Methanesulfonic acid 2-[3-fluoro-5-hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-4-methylphenyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methanesulfonic acid 2-[3-benzyloxy-4-(5-benzyloxymethyl-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-5-fluorobenzyl]-4-methylphenyl ester (85 mg) in EtOH (3 mL) and EtOAc (6 mL) is added 5% Pd/C (75 mg) and the mixture is hydrogenated at 1 atm for 18 h. The catalyst is filtered and washed with EtOH (3×). Solvent is evaporated to near dryness before water and acetonitile is added to form a solution. It is then lyophilized to give the title compound: MS (M−H)−=443.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with EtOH (3×)
  3. customSolvent is evaporated
  4. additionis added
  5. customto form a solution

Sources & evidence

ORD record
ord-cbdc1907a7a54174a9d3b1a6ebd77cd2
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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