2-Methyl-2-butene → HCID 90449616, compound

HRID 1411294Notes

Reaction equation

HRID 1411294 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=3)[N:10]([C:19]([NH:21][C:22]3[S:23][C:24]([Cl:27])=[CH:25][N:26]=3)=[O:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].CC(=CC)C.P([O-])(O)(O)=[O:34].[Na+].Cl([O-])=O.[Na+].[Cl-].[NH4+]>C(O)(C)(C)C.O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:34])=[O:18])[CH:15]=3)[N:10]([C:19](=[O:20])[NH:21][C:22]3[S:23][C:24]([Cl:27])=[CH:25][N:26]=3)[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 105532-Methyl-2-buteneHCID 25517Ammonium ChlorideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 90449869HCID 90449869, compound

Product 1

HCID 90449616HCID 90449616, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

1′-Acetyl-N-(5-chlorothiazol-2-yl)-5-formylspiro[indoline-3,3′-pyrrolidine]-1-carboxamide (7.6 mg, 0.0188 mmol) was dissolved in t-butanol (1.5 mL) and water (0.5 mL). Thereafter, 2-methyl-2-butene (52 μL, 0.50 mmol), sodium dihydrogen phosphate (14 mg, 0.113 mmol) and sodium chlorite (15 mg, 0.169 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 3.3 hours. Thereafter, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and the mixed solution was then extracted with chloroform:methanol=5:1. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=5:1) to obtain the captioned compound (6.9 mg, 87%) in the form of a white solid.

Workup

  1. extractionthe mixed solution was then extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-04ff4cfc3c0a4634b39675a77862a731
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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