Benzylamine → 1,1-dimethylethyl 7-{3-oxo-3-[(phenylmethyl)amino]propanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 473861Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]=2[CH:24]=1)=[O:6].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC1C=CC=CC=1C>[O:2]=[C:3]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:12][C:11]=2[CH:24]=1)=[O:6]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1,1-dimethylethyl 7-[3-(methyloxy)-3-oxopropanoyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.86 mmol) and benzylamine (92 mg, 0.86 mmol) in o-xylene (3 mL) was stirred at 150° C. for one hour. The reaction mixture was cooled and purified directly by silica gel chromatography (50% ethyl acetate in hexanes) to give 1,1-dimethylethyl 7-{3-oxo-3-[(phenylmethyl)amino]propanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (220 mg, 60% yield). MS (EI) for C24H28N2O5: 425 (MH+).

Workup

temperatureThe reaction mixture was cooled
custompurified directly by silica gel chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-23eeb5b37ccb495b914cee62515bd7b1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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