Cesium carbonate → HCID 21050730, compound

HRID 2213343Notes

Reaction equation

HRID 2213343 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([CH3:32])[C:11]([NH:13][CH:14]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[NH:16][C:15]2=[O:31])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:39][O:40][C:41](=[O:44])[CH2:42]Br>CN(C=O)C>[CH3:39][O:40][C:41](=[O:44])[CH2:42][N:16]1[C:17]2[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=2[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:20][CH:14]([NH:13][C:11](=[O:12])[CH:10]([CH3:32])[CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:15]1=[O:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 58697529HCID 58697529, compound

Product 1

HCID 21050730HCID 21050730, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-3-(3,4-dichlorophenyl)-2-methyl-N-(2-oxo-5-phenyl-2,3-dihydro-1H-1,4benzodiazepin-3-yl)propanamide (1.0 g) was dissolved in DMF and treated with cesium carbonate (2.1 g) and bromoacetic acid methyl ester (200□l), then left to stir at room temperature for 16 h. The mixture was partitioned between ethyl acetate and water and the organic layer washed (water, brine), dried (magnesium sulphate) and evaporated in vacuo. Purification by flash silica chromatography afforded {3-[3-(3,4-Dichlorophenyl)-2-methyl-propionylamino]-2-oxo-5-phenyl-2,3-dihydro-benzo[e][1,4]diazepin-1-yl}-acetic acid methyl ester.

Workup

  1. waitleft
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic layer washed (water, brine)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated in vacuo
  6. customPurification by flash silica chromatography

Sources & evidence

ORD record
ord-5f4e578ae5284f72af272a78f1faabab
Source dataset
uspto-grants-2006_09
Patent number
US07105509B2

Reaction notes

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