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

HRID 919122Notes

Reaction equation

HRID 919122 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 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 chromatography (EtOAc:PE, 0-50%)

Sources & evidence

ORD record
ord-b45adee7aa78443ba5cfe1c8ef9939d3
Source dataset
uspto-grants-2016_03
Patent number
US09272984B2

Reaction notes

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