Cesium carbonate → HCID 86757674, compound

HRID 2269823Notes

Reaction equation

HRID 2269823 reaction equation
[CH2:1]([NH:8][C:9](=[O:33])[CH:10]([NH:21][C:22](=[O:32])[C@H:23](Br)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](O)(=[S:36])[CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[CH2:1]([NH:8][C:9](=[O:33])[CH:10]([NH:21][C:22](=[O:32])[C@@H:23]([C:34](=[S:36])[CH3:35])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexaneHCID 57135847HCID 57135847, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86757674HCID 86757674, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine N,N′-dibenzyl-2-((R)-2-bromo-3-phenylpropionylamino)malonamide (0.49 g, 0.97 mmol) and thioacetic acid (0.172 mL, 2.42 mmol) in dimethylformamide (15 mL). Degas by repeated cycles of vacuum and filing with nitrogen. Add cesium carbonate (0.473 g, 1.45 mmol). After 18 hours, dilute the reaction mixture with water and extract twice with ethyl acetate. Combine the organic layers, extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 3/2 ethyl acetate/hexane to give the title compound (46%).

Workup

  1. customDegas by repeated cycles of vacuum and filing with nitrogen
  2. extractionextract twice with ethyl acetate
  3. extractionextract with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue

Sources & evidence

ORD record
ord-bfcbb8402fa1477e8325d44e7341e5ba
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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