Cesium carbonate → HCID 86757671, compound

HRID 2269816Notes

Reaction equation

HRID 2269816 reaction equation
[CH2:1]([NH:9][C:10](=[O:35])[CH:11]([NH:23][C:24](=[O:34])[C@H:25](Br)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[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:36](O)(=[S:38])[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([NH:9][C:10](=[O:35])[CH:11]([NH:23][C:24](=[O:34])[C@@H:25]([C:36](=[S:38])[CH3:37])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[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

5

Reactant 3

HCID 10796Cesium carbonateHCID 57217334HCID 57217334, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86757671HCID 86757671, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepare by the method of Example 1.4 using N,N′-diphenethyl-2-((R)-2-bromo-3-phenylpropionylamino)malonamide (0.11 g, 0.21 mmol), thioacetic acid (0.05 mL, 0.62 mmol), and cesium carbonate (0.10 g, 0.31 mmol) in dimethylformamide (8 mL). Purify by chromatography on silica gel eluting with 1/1 hexane ethyl acetate to give the title compound (92%).

Workup

  1. customPurify by chromatography on silica gel eluting with 1/1 hexane ethyl acetate

Sources & evidence

ORD record
ord-f9b9039da2a0488c81ffdcd764e7fffd
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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