Acetyl chloride → (3S,4S)-5-(4-acetyl-benzoyl)-3-amino-4-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride

HRID 1486035Notes

Reaction equation

HRID 1486035 reaction equation
C([Cl:4])(=O)C.C(OC(=O)[NH:11][C@H:12]1[C@H:18]([CH3:19])[N:17]([C:20](=[O:30])[C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=2)[C:16]2[CH:31]=[CH:32][CH:33]=[CH:34][C:15]=2[NH:14][C:13]1=[O:35])(C)(C)C>CO>[ClH:4].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[C@@H:18]([CH3:19])[C@H:12]([NH2:11])[C:13](=[O:35])[NH:14][C:15]3[CH:34]=[CH:33][CH:32]=[CH:31][C:16]2=3)=[O:30])=[CH:22][CH:23]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90082505[(2S,3S)-1-(4-acetyl-benzoyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 90082607(3S,4S)-5-(4-acetyl-benzoyl)-3-amino-4-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (1.0 ml, 14.1 mmol) was added dropwise to a solution of [(2S,3S)-1-(4-acetyl-benzoyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester (0.45 g, 1.03 mmol) in methanol at 0° C. and the reaction was allowed to warm to ambient temperature and stir for 2 h. The reaction was concentrated in vacuo to give (3S,4S)-5-(4-acetyl-benzoyl)-3-amino-4-methyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride which was used in the subsequent step without further purification (0.36 g, 100%).

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-12486b23c7894808a4684e595db53af5
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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