TBAF tetrahydrofuran → HCID 68106416, compound

HRID 1184365Notes

Reaction equation

HRID 1184365 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:11][CH2:10][N:9]([S:12]([NH:15][C:16]([C:18]2[N:19]=[C:20]([CH2:23][N:24]([C:34](=[O:46])[C:35]3[CH:40]=[C:39]([O:41][CH3:42])[C:38]([CH3:43])=[C:37]([O:44][CH3:45])[CH:36]=3)[CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:21][CH:22]=2)=[O:17])(=[O:14])=[O:13])[CH2:8]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH3:42][O:41][C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([O:44][CH3:45])[C:38]=1[CH3:43])[C:34]([N:24]([CH2:23][C:20]1[S:21][CH:22]=[C:18]([C:16]([NH:15][S:12]([N:9]2[CH2:10][CH2:11][CH:7]([OH:6])[CH2:8]2)(=[O:14])=[O:13])=[O:17])[N:19]=1)[CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:46]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 68106574HCID 68106574, compound

Product 1

HCID 68106416HCID 68106416, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[(3-{[tert-Butyl (dimethyl)silyl]oxy}pyrrolidin-1-yl)sulfonyl]-2-{[(3,5-dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]methyl}-1,3-thiazole-4-carboxamide (580 mg) was added to THF (10 mL), and subsequently, a 1 M TBAF/THF solution (2.02 mL) was added dropwise thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was neutralized by the addition of an appropriate amount of 1 M hydrochloric acid, and then extracted with CHCl3 several times. The organic layer was washed with brine and dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3:MeOH=20:1) to obtain 2-{[(3,5-dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]methyl}-N-[(3-hydroxypyrrolidin-1-yl)sulfonyl]-1,3-thiazole-4-carboxamide (383 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was neutralized by the addition of an appropriate amount of 1 M hydrochloric acid
  3. extractionextracted with CHCl3 several times
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (CHCl3:MeOH=20:1)

Sources & evidence

ORD record
ord-841a1ce6900849f084c246a723050290
Source dataset
uspto-grants-2014_03
Patent number
US08669246B2

Reaction notes

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