Water → tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate

HRID 415535Notes

Reaction equation

HRID 415535 reaction equation
[NH2:1][C@@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].Cl[C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[N+]([O-])=O)=[CH:21][CH:20]=[CH:19][CH:18]=2.C([N:29](CC)CC)C.[OH2:34].[Cl-].[Na+].[OH2:37]>C(Cl)Cl>[N+:29]([C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[NH:1][C@@H:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[CH:21][CH:20]=[CH:19][CH:18]=2)([O-:37])=[O:34]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 45072492tert-butyl N-((2S)-2-aminopropyl)carbamateHCID 57417360Sodium chloride; waterHCID 66619887HCID 66619887, compound

Product 1

HCID 86624122tert-Butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2S)-2-aminopropylcarbamate (2.14 g, 12.28 mmol) in 120 mL of dry CH2Cl2 was cooled to 0° C. and treated with 3-chloro-4-nitroquinoline (2.56 g, 12.28 mmol) and triethylamine (3.4 mL, 25 mmol) under an atmosphere of N2. The reaction was allowed to slowly warm to ambient temperature overnight. It was then treated with 100 mL of H2O (2×) followed by brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give tert-butyl (2S)-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate (4.10 g) as a bright yellow solid.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3e6ea95fdb046b0bddb2cd32c6d03e5
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

Loading…