Dimethylformamide → HCID 86757826, compound

HRID 276118Notes

Reaction equation

HRID 276118 reaction equation
[CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6](=[O:24])[C@@H:7]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br)[NH:8][C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12].CN(C)C=O.[C:38](O)(=[S:40])[CH3:39].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.ClCCl>[CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:5][C:6](=[O:24])[C@H:7]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:38](=[S:40])[CH3:39])[NH:8][C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86757827HCID 86757827, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86757826HCID 86757826, compound

Reagents, catalysts & solvents 1

HCID 21584124Propan-2-one--dichloromethane (1/1)Solvent3×

Procedure

Combine (R)-2-bromo-3-methylbutyroyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide (0.466 g, 0.93 mmol) and dimethylformamide (3 mL). Add thioacetic acid (0.066 mL, 0.93 mmol) and cesium carbonate (0.151 g, 0.46 mmol). After 18 hours, partition the reaction mixture between ethyl acetate and an aqueous 2 M hydrochloric acid solution. separate the layers, extract the organic layer with water and a saturated aqueous sodium bicarbonate solution, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% acetone/dichloromethane, 15% acetone/dichloromethane, and then 20% acetone/dichloromethane to give the title compound.

Workup

  1. custompartition the reaction mixture between ethyl acetate
  2. customseparate the layers
  3. extractionextract the organic layer with water
  4. dry with materiala saturated aqueous sodium bicarbonate solution, dry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-1e901ab8747448d9b58e845a2ee7ee07
Source dataset
uspto-grants-2002_03
Patent number
US06352976B1

Reaction notes

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