Diisopropylethylamine → Ethyl 2-(1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

HRID 1054215Notes

Reaction equation

HRID 1054215 reaction equation
[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20](OCC)=[O:21])[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].CCN(C(C)C)C(C)C>O1CCOCC1>[CH2:1]([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]([NH:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:21])[C:10]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 90258568Ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 118451768Ethyl 2-(1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetateYield 37%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring suspension of ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate (700 mg, 2.063 mmol), ethyl 2-aminoacetate hydrochloride (387 mg, 2.77 mmol) in dioxane (5 mL) was added DIPEA (0.660 ml, 3.78 mmol). Reaction mixture was heated at 100° C. for 12 h. Solvent from reaction mixture was distilled out to get crude product which was then column purified using 15% EtOAC in hexane to get titled product in 37% yield.

Workup

  1. customReaction mixture
  2. customSolvent from reaction mixture
  3. distillationwas distilled out
  4. customto get crude product which
  5. customcolumn purified

Sources & evidence

ORD record
ord-ca2b0b88338242f0afdf6a1397fae676
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

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