Cesium carbonate → 5-(N-Boc-Amino)-7-(methoxyacetyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

HRID 2121497Notes

Reaction equation

HRID 2121497 reaction equation
[C:1]([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)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:25]([O-:28])([O-])=O.[Cs+].[Cs+].[C:31]([O:34][CH2:35]Br)(=O)C>CN(C=O)C.C(Cl)Cl>[C:1]([NH:8][N:9]1[C:15](=[O:16])[CH:14]([C:25](=[O:28])[CH2:31][O:34][CH3:35])[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)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 114935485-(N-Boc-amino)-5,7-dihydro-6H-dibez[b,d]azepin-6-one

Product 1

HCID 223126215-(N-Boc-Amino)-7-(methoxyacetyl)-5,7-dihydro-6H-dibenz[b,d]azepin-6-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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-E) in DMF was treated with Cs2CO3 (1.10 g, 3.39 mmol) and warmed to 60° C. To the reaction mixture was added bromomethyl acetate (0.321 mL, 3.39 mmol) (Aldrich) and stirring continued for 17 hours. 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-bec06c702fb747c9bc56359736a69f78
Source dataset
uspto-grants-2004_02
Patent number
US06696438B2

Reaction notes

Loading…