Lithium Hydroxide → HCID 56644272, compound

HRID 406172Notes

Reaction equation

HRID 406172 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+]>C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:13]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:12][CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66665908HCID 66665908, compound

Product 1

HCID 56644272HCID 56644272, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Ethyl 7-(6,7-diphenyl-3,4-dihydro-1,8-naphthyridin-1(2H)-yl)heptanoate (step 1) (100 mg, 0.226 mmol) and lithium hydroxide (37.9 mg, 0.904 mmol) in THF (2 ml) was heated at 75° C. for 6 h. The reaction was quenched with water and the pH was adjusted to pH 3-4 by addition of 1M HCl. The mixture was partitioned between EtOAc and water. The organic portion was separated and washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 3:2 iso-hexane/EtOAc afforded the title compound.

Workup

  1. customThe reaction was quenched with water
  2. additionthe pH was adjusted to pH 3-4 by addition of 1M HCl
  3. customThe mixture was partitioned between EtOAc and water
  4. customThe organic portion was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the crude product by chromatography on silica eluting with 3:2 iso-hexane/EtOAc

Sources & evidence

ORD record
ord-f2e0bb4d9a5e4657a2383913f80d952c
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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