Ammonia → HCID 22181096, compound

HRID 1268204Notes

Reaction equation

HRID 1268204 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24]([OH:26])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C([N:37](CC)CC)C.N>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24](=[O:26])[NH2:37])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22181141HCID 22181141, compound

Product 1

HCID 22181096HCID 22181096, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carboxynitrobenzene (0.9 g) in dichloromethane (20 ml) were added isobutyl chloroformate (0.3 ml) and triethylamine (0.4 ml) in an ice bath and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added 28% aqueous ammonia (0.2 ml) and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/methanol=19/1 as an eluant to give the desired compound (0.9 g, yield 98%) as a pale yellow amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9fa5bf34618b42478e1542e5fa25860b
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…