Dimethylformamide → HCID 86757670, compound

HRID 2269814Notes

Reaction equation

HRID 2269814 reaction equation
[CH2:1]([NH:9][C:10](=[O:31])[CH:11]([NH:23][C:24](=[O:30])[C@H:25](Br)[CH:26]([CH3:28])[CH3:27])[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:32](O)(=[S:34])[CH3:33].CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C(OC(=O)C)C.CCCCCC>[CH2:1]([NH:9][C:10](=[O:31])[CH:11]([NH:23][C:24](=[O:30])[C@@H:25]([C:32](=[S:34])[CH3:33])[CH:26]([CH3:28])[CH3:27])[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 57206008HCID 57206008, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86757670HCID 86757670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine N,N′-diphenethyl-2-((R)-2-bromo-3-methylbutyrylamino)malonamide (0.20 g, 0.41 mmol), thioacetic acid (0.08 mL, 1.1 mmol), and dimethylformamide (8 mL). Degas by repeated cycles of vacuum and filling with nitrogen gas. Add cesium carbonate (0.215 g, 0.664 mmol). After 18 hours, dilute with water and extract with ethyl acetate. Extract the organic layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 hexane ethyl acetate to give the title compound.

Workup

  1. customDegas by repeated cycles of vacuum
  2. extractionextract with ethyl acetate
  3. extractionExtract the organic layer with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-0df41dd5289241f3a46dc98a0a1c72c2
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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