Imidazole → tert-butyl 2-(2-hydroxy-N-methylbenzamido)ethylcarbamate

HRID 1027650Notes

Reaction equation

HRID 1027650 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].N1C=CN=C1.C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C>[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([N:2]([CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:9])[CH3:11])[CH3:1])=[O:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 74041Salicyloyl chlorideHCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

Product 1

HCID 59193319tert-butyl 2-(2-hydroxy-N-methylbenzamido)ethylcarbamateYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 2-(methylamino)ethylcarbamate (0.348 g, 2 mmol), 2-hydroxybenzoyl chloride (0.276 g, 2 mmol) and imidazole (0.136 g, 2 mmol) in ethyl acetate (8 mL) at 0° C. was slowly added a solution of DCC (0.412 g, 2 mmol) in ethyl acetate (2 mL). The mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether (20-50%) to afford tert-butyl 2-(2-hydroxy-N-methylbenzamido)ethylcarbamate (0.2 g, 34%) as a colorless oil. 1HNMR (CDCl3): δ7.5 (m, 2H, CH), 7.0 (d, 1H, CH), 6.8 (d, 1H, CH), 3.7 (m, 2H, CH2), 3.48 (m, 2H, CH2), 3.2 (m, 3H, CH3), 1.5 (s, 9H, CH3).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by chromatography on silica gel
  4. washeluting with ethyl acetate/petroleum ether (20-50%)

Sources & evidence

ORD record
ord-184111db490b425bba05e7413abbf599
Source dataset
uspto-grants-2014_05
Patent number
US08735379B2

Reaction notes

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