1-Hydroxybenzotriazole → tert-Butyl 2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

HRID 1253870Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C1C=CC2N(O)N=NC=2C=1>C1(C)C=CC=CC=1>[C:9]([O:8][C:6]([N:5]1[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][C:3](=[O:2])[CH2:4]1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of [(2-amino-benzyl)-tert-butoxycarbonyl-amino]acetic acid methyl ester (640 mg, 2.18 mmol) in toluene (30 mL), was added HOBT (177 mg, 1.31 mmol). The reaction mixture was heated at 100° C. for 24 h. After the completion of reaction, as confirmed by TLC, the solvent was removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 7:13 EtOAc:Pet. Ether) to afford pure 2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester: (350 mg, 61%) as a solid.

Workup

customAfter the completion of reaction
customthe solvent was removed in vacuo
customto afford the crude compound, which
customwas purified by column chromatography (silica gel, 7:13 EtOAc:Pet. Ether)

Sources & evidence

ORD record: ord-9cc309e13bef49dc957424c026541a33
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455479B2

Reaction notes

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