2-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylate → HCID 69659809, compound

HRID 722730Notes

Reaction equation

HRID 722730 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]=[CH2:13])[NH:6]1)=[O:4].[C:14]([O:18][C:19]([NH:21][CH:22]([CH2:26][CH:27]=[CH2:28])[C:23](O)=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15].CC(COC1N(C(OCC(C)C)=O)C2C(=CC=CC=2)C=C1)C>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]=[CH2:13])[N:6]1[C:23](=[O:24])[CH:22]([NH:21][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:26][CH:27]=[CH2:28])=[O:4]

Participants

6

Reactant 3

HCID 1006212-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylateHCID 51661192-{[(Tert-butoxy)carbonyl]amino}pent-4-enoic acidHCID 69659486HCID 69659486, compound

Product 1

HCID 69659809HCID 69659809, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-allyl-piperidine-2-carboxylic acid methyl ester, 39, (2.1 g, 11.5 mmol), 2-tert-butoxycarbonylamino-pent-4-enoic acid (9.9 g, 46 mmol), and IIDQ (13.9 g, 46 mmol) in THF (50 mL) is stirred at rt for 24 h. The reaction is diluted with EtOAc and washed with 1N HCl, saturated NaHCO3, and brine. The solution is then dried (MgSO4), concentrated, and purified by flash chromatography over silica (hexanes/ethyl acetate) to afford 1.1 g of the desired product. 1H NMR (CDCl3) δ 5.76 (m, 2H), 5.60–4.20 (series of m, 8H), 3.71 (s, 3H), 2.60–1.50 (series of m, 10H), 1.44 (s, 9H).

Workup

  1. washwashed with 1N HCl, saturated NaHCO3, and brine
  2. dry with materialThe solution is then dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography over silica (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-331468af708f44f3830d71f2c9f0fd81
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

Loading…