Acetyl chloride → methyl(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclo hexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421951Notes

Reaction equation

HRID 421951 reaction equation
[Cl-].[CH2:2]([NH+:9]([CH3:41])[CH2:10][CH2:11][O:12][C@H:13]1[CH2:20][N:19]2[C:21]3[CH:22]=[C:23]([C:34]([OH:36])=[O:35])[CH:24]=[CH:25][C:26]=3[C:27]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:18]2[C:17]2[CH:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:42](Cl)(=O)C>CO>[CH2:2]([N:9]([CH3:41])[CH2:10][CH2:11][O:12][C@H:13]1[CH2:20][N:19]2[C:21]3[CH:22]=[C:23]([C:34]([O:36][CH3:42])=[O:35])[CH:24]=[CH:25][C:26]=3[C:27]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:18]2[C:17]2[CH:37]=[CH:38][CH:39]=[CH:40][C:16]=2[O:15][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86627892N-benzyl-2-{[(7S)-11-carboxy-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]oxy}-N-methylethanaminium chloride

Product 1

HCID 66674447methyl(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclo hexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (0.014 M) of N-benzyl-2-{[(7S)-11-carboxy-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl]oxy}-N-methylethanaminium chloride in anhydrous MeOH was treated with acetyl chloride (1.1 eq.). The mixture was heated at reflux overnight. All the volatiles were removed in vacuo to afford the title compound. The product was used in the next step without further purification. (ES+) m/z 553 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customAll the volatiles were removed in vacuo

Sources & evidence

ORD record
ord-16026b56f4684d1b95486b0b06bb0902
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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