Potassium Carbonate → Tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate

HRID 333135Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.CC1C=CC(S(O[CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][N:35]=[N+:36]=[N-:37])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:35]([CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:6][CH:7]=1)=[N+:36]=[N-:37]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of tert-butyl 4-hydroxyphenylcarbamate (1.24 g, 5.93 mmol), 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (1.50 g, 4.56 mmol) and K2CO3 (2.45 g, 17.79 mmol) in acetonitrile was stirred at 80° C. overnight. The reaction mixture was filtered and washed with acetonitrile. After the solvent was evaporated, the reaction mixture was diluted with DCM. The DCM solution was washed with sat. K2CO3 aqueous solution and brine. The organic phase was dried, and concentrated in vacuo to afford tert-butyl 4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenylcarbamate (1.88 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 6.35 (s, 1H), 4.10 (t, J=4.8 Hz, 2H), 3.85 (t, J=4.8 Hz, 2H), 3.76-3.62 (m, 6H), 3.39 (t, J=5.2 Hz, 2H), 1.52 (s, 9H); MS (ESI), 389 (M+Na)+.

Workup

filtrationThe reaction mixture was filtered
washwashed with acetonitrile
customAfter the solvent was evaporated
additionthe reaction mixture was diluted with DCM
washThe DCM solution was washed with sat. K2CO3 aqueous solution and brine
customThe organic phase was dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-83ddab5fa379415f8605fc81298dedcf
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877970B2

Reaction notes

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