TBAF tetrahydrofuran → HCID 68106416, compound

HRID 2409602Notes

Reaction equation

HRID 2409602 reaction equation
[Si]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([NH:17][C:18]([C:20]2[N:21]=[C:22]([CH2:25][N:26]([C:36](=[O:48])[C:37]3[CH:42]=[C:41]([O:43][CH3:44])[C:40]([CH3:45])=[C:39]([O:46][CH3:47])[CH:38]=3)[CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:23][CH:24]=2)=[O:19])(=[O:16])=[O:15])[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH3:44][O:43][C:41]1[CH:42]=[C:37]([CH:38]=[C:39]([O:46][CH3:47])[C:40]=1[CH3:45])[C:36]([N:26]([CH2:25][C:22]1[S:23][CH:24]=[C:20]([C:18]([NH:17][S:14]([N:11]2[CH2:12][CH2:13][CH:9]([OH:8])[CH2:10]2)(=[O:16])=[O:15])=[O:19])[N:21]=1)[CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:48]

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-a05f9c0a11c84c8f97e3b9b115141e61
Source dataset
uspto-grants-2014_08
Patent number
US08815920B2

Reaction notes

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