Hydrochloric Acid → 5-[(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrazinecarboxylic acid

HRID 222663Notes

Reaction equation

HRID 222663 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]([O:13][C:14]2[CH:31]=[CH:30][C:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22][C:16]=3[CH:15]=2)=[N:11][CH:12]=1)=[O:6].Cl.O>CC(C)=O>[CH3:29][C:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][C:17]2[CH:30]=[CH:31][C:14]([O:13][C:10]3[N:11]=[CH:12][C:7]([C:5]([OH:6])=[O:4])=[N:8][CH:9]=3)=[CH:15][C:16]=2[CH2:22][CH2:21]1)=[O:24])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 589845771,1-Dimethylethyl 7-({5-[(methyloxy)carbonyl]-2-pyrazinyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 574376215-[(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-2-pyrazinecarboxylic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2M Sodium hydroxide solution (110 ml) was added to a solution of 1,1-dimethylethyl 7-({5-[(methyloxy)carbonyl]-2-pyrazinyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (D49, Step 1) (29.38 g, 73.6 mmol) in acetone (480 ml) and the resulting mixture was stirred at room temperature for 25 minutes. The mixture was acidified with 2M hydrochloric acid and then poured into water (2 L). The resulting white solid was collected by filtration, washed with water and dissolved in ethyl acetate (1 L). This solution was dried under sodium sulfate and evaporated in vacuo to give the title compound (27.3 g); MS (ES+) m/e 384 [M−H]+.

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed with water
  3. dissolutiondissolved in ethyl acetate (1 L)
  4. customThis solution was dried under sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fbfd0c7a52ed4443ad8dada663a8ede9
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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