Sodium Hydroxide → (E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid

HRID 660630Notes

Reaction equation

HRID 660630 reaction equation
C[O:2][C:3](=[O:32])/[C:4](/[NH:28][C:29](=[O:31])[CH3:30])=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][C:15](=[O:17])[NH:14][S:13]2(=[O:19])=[O:18])=[C:8]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:7]=1.[OH-].[Na+]>>[C:29]([NH:28]/[C:4](=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][C:15](=[O:17])[NH:14][S:13]2(=[O:19])=[O:18])=[C:8]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:7]=1)/[C:3]([OH:32])=[O:2])(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 68838965(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid Methyl Ester

Product 1

HCID 68840076(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid

Procedure

To a solution of (E)-2-acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic acid methyl ester is added 3 equivalents of NaOH (3N solution). After 4 h, three additional equivalents of NaOH is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and the residue acidified with 1N HCl and the mixture is extracted with EtOAc. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound. This is used directly in the next step.

Workup

  1. waitis continued for 18 h
  2. customThe solvent is removed under reduced pressure
  3. extractionthe mixture is extracted with EtOAc
  4. washThe organic phase is washed with water and brine
  5. dry with materialthen is dried over sodium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-79c526d3df8146e3b9a50674774fa1c2
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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