1,4-Dioxane hydrochloride → (S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid

HRID 1291787Notes

Reaction equation

HRID 1291787 reaction equation
C([O:5][C:6](=[O:25])[C@H:7]([CH2:21][C:22](=[O:24])[NH2:23])[NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)=[O:10])(C)(C)C.Cl.O1CCOCC1>O1CCOCC1>[N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:9]([NH:8][C@H:7]([C:6]([OH:25])=[O:5])[CH2:21][C:22](=[O:24])[NH2:23])=[O:10]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 54175058Quinoline-2-carbonyl-(L)-asparagine tert-butyl Ester

Product 1

HCID 11044384(S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere, 4.0 g (11.6 mmol) of quinoline-2-carbonyl-(L)-asparagine tert-butyl ester are dissolved in 40 ml of dioxane, and 40 ml of 4N HCl/dioxane are added. On stirring for 17 h at RT, the product is precipitated in the form of a solid. Filtration and washing with DIPE yields the pure title compound: 1H-NMR (200 MHz, CD3OD): 3.02 (d, J=6 Hz, 2H), 5.09 (t, J=6 Hz, 1H), 7.92 (m, 1H), 8.12 (m, 1H), 8.26 (m, 1H), 8.4 (m, 2H), 9.03 (m, 1H).

Workup

  1. customthe product is precipitated in the form of a solid
  2. filtrationFiltration
  3. washwashing with DIPE

Sources & evidence

ORD record
ord-d946c73b820b46e5b53680a408077ff3
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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