Water → HCID 54118455, compound

HRID 583429Notes

Reaction equation

[CH3:1]I.[C:3]([O:7][C:8](=[O:27])[NH:9][CH:10]([CH2:24][C:25]#[N:26])[CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].O>CN(C)C=O>[C:3]([O:7][C:8](=[O:27])[N:9]([CH:10]([CH2:24][C:25]#[N:26])[CH:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:1])([CH3:5])([CH3:4])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

5.2 ml (82.9 mmol) of methyl iodide is added to a solution of 18.5 g (54.9 mmol) of (1-Cyanomethyl-2,2-diphenyl-ethyl)-carbamic acid tert-butyl ester in 100 ml of N,N-dimethyl-formamide, and the mixture is cooled to 0° C. 2.6 g (60.6 mmol) of 55% sodium hydride is added in several portions. After 1 h the mixture is warmed to RT and 75 ml of N,N-dimethylformamide is added for further dilution. After a total of 3.5 h the reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over sodium sulfate and concentrated by evaporation. The title compound is obtained in the form of an orange-brown mass. TLC: ethyl acetate/hexane (1:4) Rf =0.35; Rt (HPLC)=20.0 min; 1H-NMR (300 MHz, CDCl3, RT) d 7.39-7.17 (m, 10H), 5.60-5.15 (m, 1H), 4.36-3.96 (m, 1H), 2.73/2.68 (s, 3H), 2.05 (m, 2H), 1.55/1.41 (s, 9H).

Workup

temperatureAfter 1 h the mixture is warmed to RT
extractionextracted with ethyl acetate
washThe organic phase is washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-993f8491d07e4fe39f22e9e775436c8e
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929067

Reaction notes

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