1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67999849, compound

HRID 932092Notes

Reaction equation

HRID 932092 reaction equation
[CH2:1]([C@@:4]1([CH3:37])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH2:32]Cl)(=[O:29])=[O:28])[C:5]1=[O:36])[CH:2]=[CH2:3].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH2:1]([C@@:4]1([CH3:37])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:34][CH3:35])[CH2:25][N:26]2[CH2:32][CH2:31][CH2:30][S:27]2(=[O:29])=[O:28])[C:5]1=[O:36])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68001216HCID 68001216, compound

Product 1

HCID 67999849HCID 67999849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butyl)-3-chloropropane-1-sulfonamide prepared above in Step A (36.1 mg, 0.062 mmol) in DMF (1.2 mL) was added DBU (46.4 μL, 0.308 mmol) at rt. After being stirred at rt overnight, the reaction was quenched (10% citric acid), extracted (3×EtOAc), and washed (saturated aq. NaHCO3 and sat. aq. NaCl solution). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to provide the title compound as a pale brown film.

Workup

  1. customthe reaction was quenched (10% citric acid)
  2. extractionextracted (3×EtOAc)
  3. washwashed (saturated aq. NaHCO3 and sat. aq. NaCl solution)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4751cd7408c4635acb88ae42d5bf732
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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