Iodoethane → HCID 67999420, compound

HRID 932229Notes

Reaction equation

HRID 932229 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[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]([CH:31]2[CH2:33][CH2:32]2)[CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:5]1=[O:34])[CH:2]=[CH2:3].[H-].[Na+].I[CH2:39][CH3:40]>CN(C=O)C.CCOC(C)=O>[CH2:1]([C@@:4]1([CH3:35])[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:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C@@H:24]([CH:31]2[CH2:33][CH2:32]2)[CH2:25][N:26]([CH2:39][CH3:40])[S:27]([CH3:30])(=[O:29])=[O:28])[C:5]1=[O:34])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 68000053HCID 68000053, compound

Product 1

HCID 67999420HCID 67999420, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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)-2-cyclopropylethyl)methanesulfonamide (Example 289, Step A, 86 mg, 0.161 mmol) in DMF (1.5 ml) was added sodium hydride (16.06 mg, 0.401 mmol) at rt and the reaction was stirred at rt for 30 minutes. To this reaction was added iodoethane (0.058 mL, 0.723 mmol) and the reaction was stirred at rt for 2 hours. The reaction was diluted with EtOAc, washed with water and sat. NaCl, dried with Na2SO4 and then concentrated. The crude was used on next reaction.

Workup

  1. stirringthe reaction was stirred at rt for 2 hours
  2. washwashed with water and sat. NaCl
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude was used on next reaction

Sources & evidence

ORD record
ord-9e290a47badb48f4bcb3e7ba4e8d54ee
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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