Dimethylformamide → HCID 67695547, compound

HRID 1456640Notes

Reaction equation

HRID 1456640 reaction equation
CC(OC(=O)NC[CH:9]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:13]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:12]=2[NH:11][C:10]1=[O:28])(C)C.[C:30](=[O:33])([O-:32])[O-].[Cs+].[Cs+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C[N:44]([CH3:47])C=O>C(OCC)(=O)C>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][N:11]1[C:12]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:13]=2[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:15][CH:9]([NH:44][CH2:47][C:30]([O:32][C:13]([CH3:23])([CH3:14])[CH3:12])=[O:33])[C:10]1=[O:28])[CH3:42]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 67695538HCID 67695538, compound

Product 1

HCID 67695547HCID 67695547, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of rac-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-2-oxo-1H-1-benzazepin-3-yl]methylcarbamic acid 1,1-dimethylethyl ester (1.346 g, 3.11 mmole) in 17 mL of dimethylformamide was treated with cesium carbonate (1.85 g, 5.68 mmole) and ethyl bromoacetate (0.65 mL, 5.86 mmole). After stirring at ambient temperature for 3 hours, the mixture was diluted with ethyl acetate (150 ml). The organic phase was washed four times with water and once with brine, dried (sodium sulfate) and concentrated. The crude material was chromatographed by flash chromatography, eluting with 40:60 ethyl acetate-hexane, to give 1.506 g (93%) of the title compound. Mass spec. (EI, m/z 518).

Workup

  1. washThe organic phase was washed four times with water
  2. dry with materialonce with brine, dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe crude material was chromatographed by flash chromatography
  5. washeluting with 40:60 ethyl acetate-hexane

Sources & evidence

ORD record
ord-c40faed5e56d4f8fae71180a26592476
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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