Hydrochloric Acid → (3S,4S)-3-amino-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride

HRID 1486091Notes

Reaction equation

HRID 1486091 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[C@@H:10]([NH:14]C(=O)OC(C)(C)C)[C@H:9]([CH3:22])[N:8]([C:23]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])[C:7]=2[CH:31]=1)#[N:2].[ClH:32]>O1CCOCC1>[ClH:32].[NH2:14][C@@H:10]1[C:11](=[O:13])[NH:12][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:31][C:7]=2[N:8]([C:23]([CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])[C@H:9]1[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118292648tert-butyl(2S,3S)-8-cyano-2-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Product 1

HCID 90082569(3S,4S)-3-amino-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(2S,3S)-8-cyano-2-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (289 mg, 674 μmol) in 4 M HCl in dioxane (3.37 ml) was stirred for 1 h. The reaction was diluted with Et20 and the solids were collected by vacuum filtration to provide (3S,4S)-3-amino-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (218 mg, 89%) as a white solid.

Workup

  1. additionThe reaction was diluted with Et20
  2. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-7c83f2e8fe7d41a9acf660aac8afcfc6
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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