Salicylic Acid → HCID 47456092, compound

HRID 1296238Notes

Reaction equation

HRID 1296238 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C1COCC1.C(Cl)Cl>[C:17]([O:16][C:15](=[O:21])[NH:14][CH2:13][CH2:12][NH:11][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 338Salicylic AcidHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47456092HCID 47456092, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of salicylic acid (2.0 g, 14.5 mmol) and t-butyl N-(2-aminoethyl)carbamate (2.32 g, 14.5 mmol) in dry THF (15 mL) was added a solution of 1,3-dicyclocarbodiimide (3.29 g, 16.0 mmol) in CH2Cl2 (5 mL) dropwise at 0° C. The reaction was stirred for 18 h and then filtered. The filtrate was conc in vacuo. The residue was dissolved in EtOAc (50 mL), washed with 5% NaHCO3, dried with MgSO4, and conc in vacuo to a white solid. The solid purified by silica gel chromatography (gradient: 0–70% EtOAc in hexanes) to yield 2.88 grams (71%) of the product as white solid.

Workup

  1. filtrationfiltered
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with 5% NaHCO3
  4. dry with materialdried with MgSO4
  5. customThe solid purified by silica gel chromatography (gradient: 0–70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-de61355b132a4619aa4dd2f8601e8fc9
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

Loading…