Salicylic Acid → Benzyl 2-(2-hydroxybenzamido)ethylcarbamate

HRID 85356Notes

Reaction equation

HRID 85356 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CN=C1.[C:20](O)(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C>[OH:23][C:22]1[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=1[C:20]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:28]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 795ImidazoleHCID 10868DicyclohexylcarbodiimideHCID 2794257Benzyl N-(2-aminoethyl)carbamate

Product 1

HCID 59193325Benzyl 2-(2-hydroxybenzamido)ethylcarbamateYield 68.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of benzyl 2-aminoethylcarbamate (1.65 g, 8.5 mmol), imidazole (0.58 g, 8.5 mmol), salicylic acid (1.73 g, 8.5 mmol) in ethyl acetate (30 mL) was added a solution of DCC (1.75 g, 8.5 mmol) in ethyl acetate (50 mL). The mixture was stirred (RT, 16 h) and filtered. The solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (EtOAc-PE, 0-50%) to afford benzyl 2-(2-hydroxybenzamido)ethylcarbamate as a white solid (1.84 g, 66%). Mass calculated for C17H18N2O4=314.34; found: [M+H]+=315.2.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe crude product was purified by silica gel chromatography (EtOAc-PE, 0-50%)

Sources & evidence

ORD record
ord-32d11ccb495648d5a8fad9eb2b77cd53
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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