Water → HCID 46893417, compound

HRID 1519480Notes

Reaction equation

HRID 1519480 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([O:6][CH:7]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[CH3:31])[C:9]2[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:8]1=2)=[O:5].[C:38](=O)([O:48]C1C=CC([N+]([O-])=O)=CC=1)[O:39][CH2:40][CH:41]1[CH:45]([CH3:46])[O:44][C:43](=[O:47])[O:42]1.O>CN(C=O)C>[CH3:1][N:2]([CH2:3][C:4]([O:6][CH:7]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][C:16]=2[CH3:31])[C:9]2[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:8]1=2)=[O:5])[C:38]([O:39][CH2:40][C:41]1[O:42][C:43](=[O:47])[O:44][C:45]=1[CH3:46])=[O:48]

Participants

5

Reactant 3

HCID 962WaterHCID 66733165HCID 66733165, compoundHCID 66733485HCID 66733485, compound

Product 1

HCID 46893417HCID 46893417, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl methylaminoacetate (0.34 g, 0.65 mmol), and (5-methyl-1,3-dioxolane-2-one-4-yl)-methyl 4-nitrophenyl carbonate (0.22 g, 0.74 mmol) were dissolved in DMF (5 ml), and the mixture was stirred at room temperature over night. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, an aqueous saturated sodium chloride solution, and then dried over sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (n-hexane:ethyl acetate) to obtain 0.44 g (43%) of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} [methyl-(5-methyl-2-oxo-1,3-dioxol-4-yl-methoxycarbonyl)-amino]acetate as amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and then dried over sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-7b1a0d2396654b838d180ab25e125e0f
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

Loading…