tert-Butanol → 2-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl)ethyl carbamic acid tert-butyl ester

HRID 68948Notes

Reaction equation

C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([OH:22])([CH3:21])([CH3:20])[CH3:19].C1[CH2:27][O:26]CC1.[CH2:28]([N:30]1[C:36](=[O:37])[C:35]([CH3:39])([CH3:38])[C:34](=[O:40])[N:33]([CH3:41])[C:32]2[CH:42]=[C:43]([CH2:46][CH2:47]C(O)=O)[CH:44]=[CH:45][C:31]1=2)[CH3:29]>C(N(CC)CC)C>[C:18]([O:22][C:27](=[O:26])[NH:15][CH2:47][CH2:46][C:43]1[CH:44]=[CH:45][C:31]2[N:30]([CH2:28][CH3:29])[C:36](=[O:37])[C:35]([CH3:39])([CH3:38])[C:34](=[O:40])[N:33]([CH3:41])[C:32]=2[CH:42]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

Diphenylphosphoryl azide (1.0 ml) and tert-butanol (10 ml) were added to a THF solution (10 ml) of 3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yl) propionic acid (0.97 g) and triethylamine (0.67 ml). The mixture was stirred at 100° C. overnight. The reaction liquid was cooled to room temperature, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50). The purified product was condensed under reduced pressure to give the title compound (0.38 g) as a colorless oily matter.

Workup

customThe reaction liquid
temperaturewas cooled to room temperature
customcondensed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20→50:50)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-cb99989ca4f44a509d53ea07532888b2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

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