Cesium carbonate → HCID 57189547, compound

HRID 2269833Notes

Reaction equation

HRID 2269833 reaction equation
[CH2:1]([NH:9][C:10](=[O:43])[CH:11]([NH:23][C:24](=[O:42])[C@@H:25](Br)[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[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.[CH3:44][O:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][SH:51])=[CH:48][CH:47]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([NH:9][C:10](=[O:43])[CH:11]([NH:23][C:24](=[O:42])[C@@H:25]([S:51][CH2:50][C:49]1[CH:52]=[CH:53][C:46]([O:45][CH3:44])=[CH:47][CH:48]=1)[CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[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

6

Reactant 3

HCID 10796Cesium carbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 57272130HCID 57272130, compound

Product 1

HCID 57189547HCID 57189547, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine N,N′-diphenethyl-2-((S)-2-bromo-6-phthalimidohexanoylamino)malonamide (10 mmol), 4-methyoxybenzylmercaptan (3.48 mL, 25 mmol), and tetrabutylammonium iodide (about 50 mg) in dimethylformamide (10 mL). Degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add cesium carbonate (4.10 g, 12.5 mmol). After 15 hours, partition the reaction mixture between water and methyl t-butyl ether, saturate the aqueous layer with sodium chloride. Extract the aqueous layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. customDegas
  2. custompartition the reaction mixture between water and methyl t-butyl ether
  3. concentrationsaturate the aqueous layer with sodium chloride
  4. extractionExtract the aqueous layer with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-8bb1e842b56f4684893f8f3a287488fc
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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