3-Aminoquinoline → HCID 21341518, compound

HRID 2185444Notes

Reaction equation

HRID 2185444 reaction equation
O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)C(C)C)(C)C.[NH2:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2.[C:36]([O:40][C:41]([NH:43][C@@H:44]([C:53](O)=[O:54])[CH2:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>ClCCl>[N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[C:26]([NH:25][C:53](=[O:54])[C@@H:44]([CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[NH:43][C:41]([O:40][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:42])[CH:27]=1

Participants

6

Reactant 4

HCID 113753-AminoquinolineHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2755954Boc-D-homophenylalanine

Product 1

HCID 21341518HCID 21341518, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (829 mg) and N,N-diisopropylethylamine (1.13 mL) were added to a solution of 3-aminoquinoline (391 mg) and N-tert-butoxycarbonyl-D-homophenylalanine (1.13 g) in dichloromethane (15 mL) at 0° C. After stirring at 0° C. for 10 min and at room temperature for 19 hr, the solvent was removed in vacuo. The residue was diluted with 10% citric acid and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogen carbonate, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform: methanol=50:1, v/v) to afford the title compound (813 mg) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.49 (s, 9H), 2.00-2.10 (m, 1H), 2.27-2.39 (m, 1H), 2.80 (t, J=7.8 Hz, 2H), 4.20-4.29 (m, 1H), 4.98-5.07 (m, 1H), 7.19-7.33 (m, 5H), 7.51-7.55 (m, 1H), 7.62 (t, J=7.8 Hz, 1H), 7.78 (d, J=8.4 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), and 8.68-8.80 (m, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with 10% citric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, saturated sodium hydrogen carbonate, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-b984e1705d054cd09cc963959474c299
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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