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

HRID 1486040Notes

Reaction equation

HRID 1486040 reaction equation
[CH3:1][C@@H:2]1[N:8]([C:9]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]=2[NH:5][C:4](=[O:21])[C@H:3]1[NH:22]C(=O)OC(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[NH2:22][C@@H:3]1[C:4](=[O:21])[NH:5][C:6]2[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=2[N:8]([C:9]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:10])[C@H:2]1[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118292727tert-butyl(2S,3S)-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 90082357(3S,4S)-3-amino-4-methyl-5-(tetrahydro-2H-pyran-4-carbonyl)-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A room temperature solution of tert-butyl(2S,3S)-2-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (205 mg, 0.51 mmol) in a 4 M solution of hydrochloric acid in dioxane (2.5 mL) was stirred for 1.5 h. After this time, the reaction mixture was concentrated in vacuo to afford (3S,4S)-3-amino-4-methyl-5-(tetrahydro-2H-pyran-4-carbonyl)-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one hydrochloride (theo. yield 173 mg) which was used without purification.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f8056afebc7d41c9b5809fed9c0d8a4e
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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