Sodium Hydroxide → HCID 86595602, compound

HRID 2117912Notes

Reaction equation

HRID 2117912 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[N:17]=[C:18]([NH:32]C(=O)C)[S:19][C:20]=2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[NH2:32][C:18]1[S:19][C:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[C:16]([CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:6](=[O:36])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13][CH:12]=2)[N:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86595601HCID 86595601, compound

Product 1

HCID 86595602HCID 86595602, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]-carbamate (230 mg), 1N—NaOH (1.09 ml) and EtOH (5 ml) were combined, and the mixture was refluxed for 16 hours. After cooled to r.t., the organic solvent was removed in vacuo. The aqueous solution was neutrallized with 1N—HCl, and extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by preparative silica gel chromatography with CHCl3/MeOH (30:1) as an eluent to give tert-butyl [4-(2-{2-amino-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]carbamate (151.2 mg) as an off-white amorphous substance.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customthe organic solvent was removed in vacuo
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative silica gel chromatography with CHCl3/MeOH (30:1) as an eluent

Sources & evidence

ORD record
ord-3e36f07a62634059b5eb021700ec6588
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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