Ammonia → HCID 18542602, compound

HRID 1268234Notes

Reaction equation

HRID 1268234 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([C:21](O)=[O:22])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH3:27])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C([N:38](CC)CC)C.N>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:20]([C:21](=[O:22])[NH2:38])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH3:27])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18542601HCID 18542601, compound

Product 1

HCID 18542602HCID 18542602, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-carboxy-2-methylnitrobenzene (4.8 g) in dichloromethane (100 ml) were added isobutyl chloroformate (1.7 ml) and triethylamine (1.8 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 (0.8 ml) and the resulting mixture was stirred for 2 hours. 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 (4.7 g, yield 97%) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours
  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-ea2a7c74504f469d8f1d5d110bd28b97
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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