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

HRID 1253870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253870
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]

Komponenten

4

Edukt 2

HCID 757711-HydroxybenzotriazoleHCID 68630241[(2-Amino-benzyl)-tert-butoxycarbonyl-amino]acetic acid methyl ester

Produkt 1

HCID 22632545tert-Butyl 2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9cc309e13bef49dc957424c026541a33
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455479B2

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