Water → HCID 58495281, compound

HRID 516232Notes

Reaction equation

HRID 516232 reaction equation
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[CH3:23].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][O:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59150535HCID 59150535, compound

Product 1

HCID 58495281HCID 58495281, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 828 mg of t-butyl 7-hydroxy-6-methyl-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 25 ml of DMF were added 0.268 ml of methyl bromoacetate and 390 mg of potassium carbonate, followed by stirring at 55° C. for 13 hours. The reaction mixture was allowed to cool, and water added, followed by extraction with EtOAc twice. The combined organic layer was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 1.076 g of t-butyl 7-(2-methoxy-2-oxoethoxy)-6-methyl-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a yellowish white solid.

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with EtOAc twice
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-6374aba5089e440e84afbd3b9aea10e4
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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