Tetrahydrofuran → HCID 91524016, compound

HRID 1246491Notes

Reaction equation

HRID 1246491 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[C:9]([NH:12][C:13]1[S:14][C:15]([C:34]([NH:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41](SC)=[CH:40][CH:39]=2)=[O:35])=[C:16]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:21]=2)[N:17]=1)(=[O:11])[CH3:10].[CH2:46]1COCC1>O>[C:9]([NH:12][C:13]1[S:14][C:15]([C:34]([NH:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([S:1]([CH3:46])(=[O:6])=[O:2])=[CH:42][CH:43]=2)=[O:35])=[C:16]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:24][CH:25]=2)[N:17]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10313463Potassium peroxymonosulphateHCID 86595599Tert-butyl (4-{2-[2-(acetylamino)-5-({[4-(methylthio)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate

Product 1

HCID 91524016HCID 91524016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium peroxymonosulfate (264 mg) was suspended in water (1 ml) and THF (1 ml), and then tert-butyl (4-{2-[2-(acetylamino)-5-({[4-(methylthio)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate (155 mg) in THF (2 ml) was added dropwise to the suspension at 0° C. The reaction mixture was stirred at r.t. for an hour, and then water was added to the suspension. The solution was extracted with AcOEt (twice). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo to give tert-butyl (4-{2-[2-(acetylamino)-5-({[4-(methylsulfonyl)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate (140.6 mg) as an off-white solid.

Workup

  1. extractionThe solution was extracted with AcOEt (twice)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85662bbc716444d18fe094f7176eb367
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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