1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one → HCID 131727232, compound

HRID 2376623Notes

Reaction equation

HRID 2376623 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:13])[C:3]1=[O:14].[C:15]1([CH3:42])[CH:20]=[CH:19][C:18]([C:21]([C@@:23]([C:39]([OH:41])=[O:40])([OH:38])[C@@:24]([C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)=[O:30])([OH:28])[C:25]([OH:27])=[O:26])=[O:22])=[CH:17][CH:16]=1>CO>[C:15]1([CH3:42])[CH:20]=[CH:19][C:18]([C:21]([C@@:23]([C:39]([OH:41])=[O:40])([OH:38])[C@@:24]([C:29]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=2)=[O:30])([OH:28])[C:25]([OH:27])=[O:26])=[O:22])=[CH:17][CH:16]=1.[NH2:1][C@H:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:13])[C:3]1=[O:14]

Participants

4

Reactant 2

HCID 210725651-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one2×HCID 29414711Di-para-toluoyl-L-tartaric acid

Product 1

HCID 131727232HCID 131727232, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

In a 22 L vessel, under nitrogen, 1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (438 g, 2.3 mol) was heated (about 40° C.) to provide a solution in methanol (4.38 mL). In another flask, di-p-toluoyl-l-tartaric acid (889.7 g, 2.3 mol) was dissolved in 4.38 L of methanol and heated to about 40° C. before the solution of 1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one was added. The heating was continued and an additional 6.13 L of methanol was added before the mixture was refluxed for about 45 minutes and then slowly cooled to ambient temperature to give a solid. After stirring for about 18 hours, the solid was collected by filtration and rinsed with a small amount of mother liquors, and after air drying, with about 2 L of ethyl acetate to give 561.6 g of (S)-1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one di-p-toluoyl-L-tartaric acid salt. Combine (S)-1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one di-p-toluoyl-L-tartaric acid salt, dichloromethane (6.57 L) and 1N aqueous sodium hydroxide solution (6.57 L) and agitate. Separate the layers and extract the organic layer twice with and 1N aqueous sodium hydroxide solution (3.28 L), once with brine (2.46 L) before drying over magnesium sulfate, filtering, and evaporating on a rotary evaporator to give the title compound 250g (57.4%, 94.1% ee).

Workup

  1. additionwas added
  2. temperaturewas refluxed for about 45 minutes
  3. customto give a solid
  4. filtrationthe solid was collected by filtration
  5. washrinsed with a small amount of mother liquors
  6. dry with materialafter air drying, with about 2 L of ethyl acetate

Sources & evidence

ORD record
ord-879cd51d68fe4f8a86aa564744f8a545
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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