Sodium Bicarbonate → HCID 66918789, compound

HRID 1367598Notes

Reaction equation

HRID 1367598 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[OH:20])=[O:4].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](OC(=N)C(Cl)(Cl)Cl)([CH3:30])[CH3:29])=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1CCCCC1.FC(F)(F)S(O)(=O)=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:11])=[O:12])[CH2:7][C@@H:6]1[O:20][C:28]([C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)([CH3:30])[CH3:29])=[O:4]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 66918607HCID 66918607, compoundHCID 66918649HCID 66918649, compound

Product 1

HCID 66918789HCID 66918789, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 6344DichloromethaneSolvent2×HCID 8078CyclohexaneSolvent

Procedure

(1R,2R,4R) and (1S,2S,4S)-4-(2-Chloro-benzenesulfonyl)-2-hydroxy-cyclopentanecarboxylic acid methyl ester (100 mg, 0.314 mmol, example 48, step 5) and 2,2,2-trichloro-acetimidic acid 1-(4-chloro-phenyl)-1-methyl-ethyl ester (270 mg, 0.514 mmol) were dissolved in a mixture of DCM (1 ml) and cyclohexane (2 ml). Then a solution of trifluoromethanesulfonic acid (0.836 μl, 0.00941 mmol) in DCM (0.1 ml) was added and the reaction mixture was stirred at room temperature for 6 h. Then saturated NaHCO3 solution was added and the mixture was extracted 3 times with ether. The combined organic layers were dried (Na2SO4) and evaporated. The remaining light yellow oil was purified by silica gel chromatography (heptane/EtOAc 4:1-3:1) to obtain the title compound (47 mg, 32%) as white solid. MS (EI): 488.1 (M+NH4)+.

Workup

  1. extractionthe mixture was extracted 3 times with ether
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. customevaporated
  4. customThe remaining light yellow oil was purified by silica gel chromatography (heptane/EtOAc 4:1-3:1)

Sources & evidence

ORD record
ord-29921b4472bb4f60aec6200763cd604e
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…