Hydrochloric Acid → HCID 69567418, compound

HRID 1777165Notes

Reaction equation

HRID 1777165 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.O[C@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.Cl>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C@@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 11776TriphenylphosphineHCID 637514(+)-Methyl lactateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 69567418HCID 69567418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of quinolin-8-ol (300 mg, 2.07 mmol) in THF (5 mL) was added (R)-methyl 2-hydroxypropanoate (215 mg, 2.07 mmol), PPh3 (647 mg, 2.47 mmol) and DEAD (430 mg, 2.47 mmol). The mixture was stirred at 25° C. for 16 hours. Subsequently, 1M HCl was added (10 mL) and the solution was washed with EtOAc (20 mL×3). The pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL), and then this solution was washed with EtOAc (10 mL×3). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was directly for the next step. LCMS (m/z): 232.1/233.1 [M+H]+

Workup

  1. washthe solution was washed with EtOAc (20 mL×3)
  2. temperatureThe pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL)
  3. washthis solution was washed with EtOAc (10 mL×3)
  4. washThe combined organic extracts were washed with brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c520b36142a24d51aac367b94f9ec8bf
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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