Sodium Hydroxide → HCID 90449654, compound

HRID 1411234Notes

Reaction equation

HRID 1411234 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:21])[CH2:16][O:17]C(=O)C)[CH2:11]3)[CH2:9][N:8]([C:22]([NH:24][C:25]3[S:26][C:27]([Cl:30])=[CH:28][N:29]=3)=[O:23])[C:5]2=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1.CO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:21])[CH2:16][OH:17])[CH2:11]3)[CH2:9][N:8]([C:22]([NH:24][C:25]3[S:26][C:27]([Cl:30])=[CH:28][N:29]=3)=[O:23])[C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 90449864HCID 90449864, compound

Product 1

HCID 90449654HCID 90449654, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-N-(5-chlorothiazol-2-yl)-1′-(2-acetoxyacetyl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (64.0 mg, 0.136 mmol) was dissolved in a mixed solvent of tetrahydrofuran (2 mL) and methanol (1 mL). Thereafter, an aqueous solution of sodium hydroxide (2 M, 0.5 mL) was added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 30 minutes. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1→7:1) to obtain the captioned compound (37.8 mg, 65%) in the form of a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:1→7:1)

Sources & evidence

ORD record
ord-ae3c210efd7d444bae5fd66ceb326774
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

Loading…