Sodium hydride → HCID 67999954, compound

HRID 932224Notes

Reaction equation

HRID 932224 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Si:9]([O:26][CH2:27][C@@H:28]([N:32]1[C@H:37]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[C@@H:36]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[CH:46]=2)[CH2:35][C@@:34]([C:53](=[CH2:58])[C:54]([O:56][CH3:57])=[O:55])([CH3:52])[C:33]1=[O:59])[CH:29]1[CH2:31][CH2:30]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O>[Si:9]([O:26][CH2:27][C@@H:28]([N:32]1[C@H:37]([C:38]2[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=2)[C@@H:36]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([Cl:51])[CH:46]=2)[CH2:35][C@@:34]([C:53]2([C:54]([O:56][CH3:57])=[O:55])[CH2:2][CH2:58]2)([CH3:52])[C:33]1=[O:59])[CH:29]1[CH2:30][CH2:31]1)([C:22]([CH3:23])([CH3:24])[CH3:25])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 68000093HCID 68000093, compound

Product 1

HCID 67999954HCID 67999954, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of trimethylsulfoxonium iodide (39 mg, 0.18 mmol) in DMSO (0.71 mL) was added a suspension of 60% sodium hydride in mineral oil (7.1 mg, 0.18 mmol). After being stirred 15 min, a solution of methyl 2-((3R,5R,6S)-1-((S)-2-(tert-butyldiphenylsilyloxy)-1-cyclopropylethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acrylate (66 mg, 0.089 mmol; Example 270, Step B) in DMSO (0.71 mL) was added and the mixture was stirred at rt for 3 h. The reaction was quenched (ice cold sat. NH4Cl), extracted (2×EtOAc), and washed (brine×3). The combined organic layers were dried (Na2SO4) and concentrated under the reduced pressure. Purification of the residue by chromatography on silica gel (4 g SiO2, 10% and 20% EtOAc/Hex) provided the title compound as a colorless film.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at rt for 3 h
  3. customThe reaction was quenched (ice cold sat. NH4Cl)
  4. extractionextracted (2×EtOAc)
  5. washwashed (brine×3)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated under the reduced pressure
  8. customPurification of the residue by chromatography on silica gel (4 g SiO2, 10% and 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-cb92c84d12564e57862365cde2fcaf1f
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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