Dichloromethane → HCID 22288340, compound

HRID 968261Notes

Reaction equation

HRID 968261 reaction equation
C([NH:8][N:9]1[C:15](=[O:16])[CH2:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=2)(OC(C)(C)C)=O.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].C(Cl)[Cl:38]>CN(C=O)C>[ClH:38].[NH2:8][N:9]1[C:15](=[O:16])[CH:14]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]1=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 114935485-(N-Boc-amino)-5,7-dihydro-6H-dibez[b,d]azepin-6-one

Product 1

HCID 22288340HCID 22288340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-(N-Boc-amino)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.03, 3.08 mmol) (Example 3) in DMF was treated with Cs2CO3 (1.10 g, 3.39 mmol) and warmed to 60° C. To this reaction mixture was added methyl bromoacetate (0.321 mL, 3.39 mmol) (Aldrich) and stirring was continued for 17 h. After cooling to 23° C., the mixture was diluted with CH2Cl2, washed with several portions of brine and dried over Na2SO4. The title compound was purified by chromatography (SiO2, CHCl3).

Workup

  1. temperatureAfter cooling to 23° C.
  2. washwashed with several portions of brine
  3. dry with materialdried over Na2SO4
  4. customThe title compound was purified by chromatography (SiO2, CHCl3)

Sources & evidence

ORD record
ord-376b608e699f4cd7a2365e4f59c39054
Source dataset
uspto-grants-2005_10
Patent number
US06958330B1

Reaction notes

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