Sodium hydride → HCID 23502986, compound

HRID 1835664Notes

Reaction equation

HRID 1835664 reaction equation
COC1C=CC(C[SH:8])=CC=1.[H-].[Na+].[C:13]1([CH2:19][CH:20]([N:28]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:31][CH:30]([NH:41][C:42](=[O:60])[CH:43](Br)[CH2:44][CH2:45][CH2:46][CH2:47][N:48]3[C:56](=[O:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:49]3=[O:58])[C:29]2=[O:61])[C:21]([O:23]C(C)(C)C)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]1([CH2:19][CH:20]([N:28]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:31][CH:30]([NH:41][C:42](=[O:60])[CH:43]([SH:8])[CH2:44][CH2:45][CH2:46][CH2:47][N:48]3[C:56](=[O:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:49]3=[O:58])[C:29]2=[O:61])[C:21]([OH:23])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 23502982HCID 23502982, compound

Product 1

HCID 23502986HCID 23502986, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Combine p-methoxybenzylmercaptan (0.08 mL, 0.57 mmol) and sodium hydride (17 mg, 60% oil dispersion, 0.42 mmol) in degassed dimethylfornamide (3 mL). After 1 hour, tetra-n-butylammonium iodide (about 5 mg) and N-[hexahydro-1-[1-(phenylmethyl)-1-t-butoxycarbonylmethyl]-2-oxo-5-phenyl-1H-azepin-3-yl]-1,3-dihydro-a-bromo-1,3-dioxo-2H-isoindole-2-hexanamide (0.20 g, 0.27 mmol). After 20 hours, quench be the addition of a saturated aqueous ammonium chloride solution and dilute with water (about 5 mL). Extract with ethyl acetate (about 75 mL). Separate the layers and extract the organic layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. waitAfter 20 hours
  2. customquench
  3. additionthe addition of a saturated aqueous ammonium chloride solution
  4. additiondilute with water (about 5 mL)
  5. extractionExtract with ethyl acetate (about 75 mL)
  6. customSeparate the layers
  7. extractionextract the organic layer with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo

Sources & evidence

ORD record
ord-83e4c848583943e58a266685e90488be
Source dataset
uspto-grants-2004_08
Patent number
US06770640B1

Reaction notes

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