Triethylamine → HCID 67548302, compound

HRID 43904Notes

Reaction equation

HRID 43904 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N(CC)CC)C.[C:19]([O:23][C:24]([NH:26][CH:27]1[CH2:30][NH:29][CH2:28]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([O:23][C:24]([NH:26][CH:27]1[CH2:28][N:29]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:30]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 15194053-Aminoazetidine, 3-BOC protected

Product 1

HCID 67548302HCID 67548302, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (0.40 mL, 2.79 mmol) and triethylamine (0.65 mL, 4.64 mmol) were added to a solution of 3-[(tert-butoxycarbonyl)amino]azetidine (400 mg, 2.32 mmol) in dichloromethane (23 mL) at room temperature, followed by stirring for 40 minutes. The reaction solution was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1) to obtain 481 mg of the title compound as a white solid (68%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-75a887d28a174090b477d534a8ed17dc
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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