Ammonia → HCID 18542597, compound

HRID 1268215Notes

Reaction equation

HRID 1268215 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]([OH:23])=O)=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:16]=2[Cl:27])[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:23])[NH2:38])=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:16]=2[Cl:27])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18542656HCID 18542656, compound

Product 1

HCID 18542597HCID 18542597, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-carboxy-3-chloronitrobenzene (2.6 g) in dichloromethane (80 ml) were added isobutyl chloroformate (1.0 ml) and triethylamine (1.1 ml) in an ice bath and the mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 28% aqueous ammonia (0.5 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 (2.2 g, yield 84%) 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-dcbab24fca8549e2b6fa5c6ede7115fb
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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