Water → tert-Butyl 2-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)ethyl carbonate

HRID 1797319Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][OH:17])[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:19].[C:27]([O:31][C:32](ONC(C1C=CC=CC=1)C#N)=[O:33])([CH3:30])([CH3:29])[CH3:28].O.CCOC(C)=O>C(N(CC)CC)C>[C:32](=[O:33])([O:17][CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][C:3]([C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])=[C:2]([Cl:1])[CH:7]=1)[O:31][C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound 102 (200 mg) was dissolved in dry triethylamine (3.0 mL) and {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile (148 mg) was added. The solution was stirred at 70° C. for 5 h. The reaction mixture was cooled to room temperature and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/diethyl ether 8:1 as the eluent to afford the title compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous phase was extracted with more EtOAc (×2)
washThe combined organic phases were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-32f21bfe390349cf8480ba3afa2da2f8
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034015B2

Reaction notes

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