Aniline → HCID 53646239, compound

HRID 1839199Notes

Reaction equation

HRID 1839199 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:16]1([NH:15][C:12]([CH:10]2[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:11]2)=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10868DicyclohexylcarbodiimideHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 53646239HCID 53646239, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-3-Azetidinecarboxylic acid 46 (0.50 g, 2.48 mmol) and aniline (274 [L, 1.1 eq.) in 5 mL of dry CH2Cl2 was added DCC (730 mg, 1.1 eq.) in one portion at 0° C. The mixture was stirred at room temperature for 3 hours. Filtration and removal of the solvent gave an oily crude product, which was purified by flash column chromatography (silica gel, hexane:ethyl acetate) to afford 1-Boc-Azetidine-3-carboxylic acid phenylamide 47 as a colorless oil (660 mg, 96%).

Workup

  1. filtrationFiltration and removal of the solvent
  2. customgave an oily crude product, which
  3. customwas purified by flash column chromatography (silica gel, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-45b5dea2ce894d4e8eb3406c18a7a5ee
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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