Hydrochloric Acid → (S)-3-amino-5-methanesulfonyl-1-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride

HRID 1372968Notes

Reaction equation

C(OC(=O)[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:9]1)(C)(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[NH2:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 100 mg (0.27 mmol) of ((S)-5-methanesulfonyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 5 ml of dioxane was treated with 0.22 ml of hydrochloric acid and heated in the sealed flask at 50° C. for 1 hour. For the working-up, the solvent was evaporated under reduced pressure and the residue submitted to a azeotropic distillation with toluene. After drying under reduced pressure, the (S)-3-amino-5-methanesulfonyl-1-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride was obtained in quantitative yield as a light yellow solid; MS: m/e=270 (M+H)+.

Workup

customthe solvent was evaporated under reduced pressure
distillationthe residue submitted to a azeotropic distillation with toluene
customAfter drying under reduced pressure

Sources & evidence

ORD record: ord-9beba4e721284c14877cc9e048306922
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160875B2

Reaction notes

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