Hydrochloric Acid → HCID 66665960, compound

HRID 2276522Notes

Reaction equation

HRID 2276522 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30].[OH-].[Li+].Cl>C1COCC1.O.O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66665424HCID 66665424, compound

Product 1

HCID 66665960HCID 66665960, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Enantiomer 2 of methyl 6-(1-methyl-6,7-diphenyl-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl)hexanoate (34 mg, 0.079 mmol) was dissolved in THF/water (2:1) and lithium hydroxide (9.99 mg, 0.238 mmol) was added. The reaction mixture was stirred vigorously at room temperature for 48 h and then diluted with water (20 ml). The pH was adjusted to pH 3-4 by addition of 2M HCl. The aqueous portion was extracted with DCM (3×30 ml) and the combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil;

Workup

  1. extractionThe aqueous portion was extracted with DCM (3×30 ml)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af9ab51b43f64b59827600d7b5b167d0
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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