Ethyl bromoacetate → HCID 19607848, compound

HRID 745116Notes

Reaction equation

HRID 745116 reaction equation
[CH3:1][NH:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[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[Cl:29])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH:4]1[OH:32].BrC[C:35](OCC)=[O:36].[CH:40](N(C(C)C)CC)(C)C>C(#N)C>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:3]3[CH:4]([O:32][C:35](=[O:36])[CH2:1][N:2]3[CH3:40])[CH2:5][CH2:6]2)=[O:31])=[CH:20][CH:19]=1)=[O:30]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 19607841HCID 19607841, compound

Product 1

HCID 19607848HCID 19607848, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-methylamino-4-hydroxy-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.13 g), ethyl α-bromoacetate (58 mg), diisopropylethylamine (49 mg) and acetonitrile (5 ml) is refluxed for 10 hours. Acetonitrile is distilled off under reduced pressure, and the resulting residue is dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1), and recrystallized from chloroform/methanol to give 7-[4-(2-chlorobenzoylamino)benzoyl]-1-methyl-1,2,3,4a,5,6,7,11b-octahydro-3-oxo[1]benzazepino[4,5-b][1,4]oxazine (80 mg) as colorless prisms, m.p. 286°-290° C.

Workup

  1. temperatureis refluxed for 10 hours
  2. distillationAcetonitrile is distilled off under reduced pressure
  3. dissolutionthe resulting residue is dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  8. customrecrystallized from chloroform/methanol

Sources & evidence

ORD record
ord-1dbd3e6b2c85423d99c24e1627a8d9f4
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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