Water → HCID 86619527, compound

HRID 1803367Notes

Reaction equation

HRID 1803367 reaction equation
[NH2:1][C@H:2]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.Cl[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=[CH:31][C:30]=1[N+:39]([O-:41])=[O:40].O>C(Cl)Cl.C(OCC)(=O)C.C(Cl)Cl>[Si:14]([O:13][CH2:12][C@@H:2]([NH:1][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=[CH:31][C:30]=1[N+:39]([O-:41])=[O:40])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 86619525HCID 86619525, compound

Product 1

HCID 86619527HCID 86619527, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

tert-Butyl (2S)-2-amino-3-{[tert-butyl(dimethyl)silyl]oxy}propylcarbamate (3.43 g, 11.3 mmol) was dissolved in 110 mL of dry CH2Cl2. Triethylamine (3.14 mL, 22.6 mmol) and 4-chloro-3-nitroquinoline (2.35 g, 11.3 mmol) were then added and the reaction was stirred under N2 overnight. The reaction mixture was then treated with 100 mL of H2O and 100 mL of CH2Cl2. The layers were separated and the organic portion was washed successively with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give yellow solid. Chromatography (SiO2, 0-20% ethyl acetate/CH2Cl2) gave tert-butyl (2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate (4.84 g) as a yellow solid.

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed successively with H2O and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give yellow solid

Sources & evidence

ORD record
ord-74218bda1dc6443c9070890e04e40bd7
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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