Hydrochloric Acid → {2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic Acid

HRID 660805Notes

Reaction equation

HRID 660805 reaction equation
C[O:2][C:3](=[O:34])[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.[OH-].[K+].Cl>O.CO.CC#N>[CH2:27]([O:26][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[N:18]1[CH2:22][C:21](=[O:23])[NH:20][S:19]1(=[O:25])=[O:24])[CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][C:3]([OH:34])=[O:2])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68838762{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic Acid Methyl Ester

Product 1

HCID 68839879{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-phenyl}-acetic Acid

Reagents, catalysts & solvents 1

HCID 21864137Acetonitrile methanol waterSolvent

Conditions

Temperature
60 °C

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 (Example 512, step C) in water/MeOH/MeCN (1:1:1) is added KOH and the mixture is heated at 60° C. for 1 h. The mixture is cooled to RT, acidified with 1N HCl and extracted with EtOAc. The organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. temperatureThe mixture is cooled to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e6351147e62b456ba9887a1dc72d4fe0
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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