Water → HCID 12114480, compound

HRID 479963Notes

Reaction equation

HRID 479963 reaction equation
C([N:8]([CH:38]1[CH2:41][N:40]([S:42]([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:47][CH:46]=2)(=[O:44])=[O:43])[CH2:39]1)[CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([O:30]CC2C=CC=CC=2)=[C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:24]=1)[O:11][Si](CC)(CC)CC)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])=O.[NH4+]>O1CCCC1.CO.[Pd]>[CH2:52]([O:51][C:48]1[CH:47]=[CH:46][C:45]([S:42]([N:40]2[CH2:39][CH:38]([NH:8][CH2:9][CH:10]([C:19]3[CH:20]=[CH:21][C:22]([OH:30])=[C:23]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:24]=3)[OH:11])[CH2:41]2)(=[O:43])=[O:44])=[CH:50][CH:49]=1)[CH2:53][CH2:54][CH3:55]

Participants

8

Reactant 4

HCID 962WaterHCID 2723923Ammonium formateHCID 2724141Tetrabutylammonium FluorideHCID 69952191HCID 69952191, compound

Product 1

HCID 12114480HCID 12114480, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[5-((1R)-2-{benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amino}-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide (0.10 g, 0.12 mmol) in tetrahydrofuran (1 ml) was added 0.2 ml of tetrabutylammonium fluoride (1 M in THF). After 2 h at room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate, and evaporated. The residue obtained was dissolved in methanol (3 ml), and treated with ammonium formate (0.12 g, 1.8 mmol) and 10% Pd/C (20 mg) at reflux for 18 h. It was then cooled to room temperature, filtered through Celite, and eluted with more methanol. The filtrate was evaporated, and the residue washed with ether-hexanes to give 55 mg of an off-white solid; m.p. 67-70° C.; MS (ES) m/z 514.0 (MH+); HRMS (FAB) Calcd. for C22H32N3O7S2 (MH+): 514.1682, Found: 514.1693.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. temperatureat reflux for 18 h
  6. filtrationfiltered through Celite
  7. washeluted with more methanol
  8. customThe filtrate was evaporated
  9. washthe residue washed with ether-hexanes

Sources & evidence

ORD record
ord-eb95e53cab4e48e29870a1122c1222aa
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

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