Hydrochloric Acid → 5-{2-Benzyloxy-4-[2-(2-hydroxyethyl)-benzyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660808Notes

Reaction equation

HRID 660808 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][C:21](=[O:23])[NH:20][S:19]2(=[O:25])=[O:24])=[C:14]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:13]=1.[Li+].[BH4-].Cl>C1COCC1>[CH2:27]([O:26][C:14]1[CH:13]=[C:12]([CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][OH:2])[CH:17]=[CH:16][C:15]=1[N:18]1[S:19](=[O:25])(=[O:24])[NH:20][C:21](=[O:23])[CH2:22]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 68838762{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic Acid Methyl Ester

Product 1

HCID 688431525-{2-Benzyloxy-4-[2-(2-hydroxyethyl)-benzyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic acid methyl ester (32 mg, 0.067 mmol) in THF (4 mL) is added LiBH4 (25 mg, 0.115 mmol) and the mixture is stirred at RT for 2 h. The mixture is cooled in an ice bath and is acidified with 1N HCl. The mixture is extracted with EtOAc and the organic phase is washed with 1N HCl and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound as a gum.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. extractionThe mixture is extracted with EtOAc
  3. washthe organic phase is washed with 1N HCl and brine
  4. dry with materialthen is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-78a5e62bf6a84e1e828975c5795c2900
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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