Trifluoroacetic acid → HCID 11591283, compound

HRID 20494Notes

Reaction equation

HRID 20494 reaction equation
C(O)(C(F)(F)F)=O.[Si]([O:15][CH2:16][C@H:17]([CH3:47])[O:18][C:19]1[CH:20]=[C:21]([CH:33]=[C:34]([O:36][C:37]2[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:39][CH:38]=2)[CH:35]=1)[C:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][O:31][CH3:32])[N:29]=1)=[O:23])(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[OH:15][CH2:16][C@H:17]([CH3:47])[O:18][C:19]1[CH:20]=[C:21]([CH:33]=[C:34]([O:36][C:37]2[CH:38]=[CH:39][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:41][CH:42]=2)[CH:35]=1)[C:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][O:31][CH3:32])[N:29]=1)=[O:23]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 593468973-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-[4-(methoxymethyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenoxy]benzamide

Product 1

HCID 11591283HCID 11591283, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-[4-(methoxymethyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenoxy]benzamide (325 mg, 0.536 mmol) in DCM (4 mL) and water (1 mL) and the reaction was stirred for 1 h. The reaction was basified to pH7-8 with saturated aqueous sodium hydrogencarbonate and then extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4), filtered and evaporated and purified by column chromatography, eluting with 50% to 100% ethyl acetate in hexanes, to afford the title compound as a white foam (147 mg, 56%).

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by column chromatography
  6. washeluting with 50% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ae020b2994ca468ea66cd5d6b4c793e7
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

Loading…