2-Thiophenesulfonamide → HCID 67999458, compound

HRID 932219Notes

Reaction equation

HRID 932219 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH:24]3[CH2:26][CH2:25]3)[CH2:22]O)[C:11](=[O:27])[C@:10]([CH2:29][C:30]([O:32][CH3:33])=[O:31])([CH3:28])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(C=P(CCCC)(CCCC)CCCC)#N.[S:50]1[CH:54]=[CH:53][CH:52]=[C:51]1[S:55]([NH2:58])(=[O:57])=[O:56]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH:24]3[CH2:25][CH2:26]3)[CH2:22][NH:58][S:55]([C:51]3[S:50][CH:54]=[CH:53][CH:52]=3)(=[O:57])=[O:56])[C:11](=[O:27])[C@:10]([CH2:29][C:30]([O:32][CH3:33])=[O:31])([CH3:28])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 728812-ThiophenesulfonamideHCID 4622928CyanomethylenetributylphosphoraneHCID 67999735HCID 67999735, compound

Product 1

HCID 67999458HCID 67999458, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-2-hydroxyethyl)-3-methyl-2-oxopiperidin-3-yl)acetate (100 mg, 0.184 mmol; Example 263, Step C) and cyanomethylenetributylphosphorane (177 μL, 0.734 mmol) in toluene (0.92 mL) was added thiophene-2-sulfonamide (90 mg, 0.55 mmol) and the resulting solution was stirred at 35° C. overnight. The reaction was quenched (sat. NH4Cl), extracted (2×EtOAc), and washed (brine). The combined organic layers were dried (Na2SO4) and concentrated under the reduced pressure. Purification of the residue by chromatography on silica gel (24 g SiO2, 35% EtOAc/Hex) provided the title compound as a pale yellow foam.

Workup

  1. customThe reaction was quenched (sat. NH4Cl)
  2. extractionextracted (2×EtOAc)
  3. washwashed (brine)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under the reduced pressure
  6. customPurification of the residue by chromatography on silica gel (24 g SiO2, 35% EtOAc/Hex)

Sources & evidence

ORD record
ord-d6aa7b47a6d9486db962cb5e45d08f6b
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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