Hydrochloric Acid → HCID 90082408, compound

HRID 1486087Notes

Reaction equation

HRID 1486087 reaction equation
[C:1]([C:3]1[CH:42]=[CH:41][C:6]2[N:7]([CH2:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][C:31]=3[CH3:40])[C:8](=[O:28])[C@@H:9]([NH:20]C(=O)OC(C)(C)C)[C@H:10]([CH3:19])[N:11]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:5]=2[CH:4]=1)#[N:2].[ClH:43]>O1CCOCC1.CCOCC>[ClH:43].[NH2:20][C@@H:9]1[C:8](=[O:28])[N:7]([CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][C:31]=2[CH3:40])[C:6]2[CH:41]=[CH:42][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:11]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C@H:10]1[CH3:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131736778tert-butyl(3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Product 1

HCID 90082408HCID 90082408, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (510 mg, 863 μmol) in 4 M HCl in dioxane (4.32 ml) was stirred for 2 h. The reaction was diluted with Et2O and the solids were collected by vacuum filtration to provide (3S,4S)-3-amino-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (410 mg, 90%) as a white solid. MS m/z 491 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-3d2dfefe59724614905889f0fac45661
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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