Acetic Acid → HCID 70976510, compound

HRID 882239Notes

Reaction equation

HRID 882239 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].[OH-].[Li+].C(O)(=O)C>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium Hydroxide2×HCID 70976575HCID 70976575, compound

Product 1

HCID 70976510HCID 70976510, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methyl 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 30)(5.23 g, 11.93 mmol) in MeOH (80 mL) was treated with aqueous lithium hydroxide (1M, 17.89 mL, 17.89 mmol) and the resulting mixture, which became a suspension after 5 min was stirred. After 24 h, lithium hydroxide (17.89 mL, 17.89 mmol) was added and the mixture (which by then was a solution) was stirred at 50° C. for 3 h. The mixture was cooled to room temperature, most of the MeOH was evaporated in vacuo and the residue treated with acetic acid (2.73 mL, 47.7 mmol). After 5 min, a precipitate formed, was isolated by filtration, washed with water and dried at 45° C. under vacuum for 16 h to give 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (4.88 g, 11.50 mmol, 96% yield) as a white solid. LCMS (HpH, 2 min), Rt=0.70 min, MH+=425.

Workup

  1. customafter 5 min
  2. stirringwas stirred at 50° C. for 3 h
  3. customwas evaporated in vacuo
  4. waitAfter 5 min
  5. customa precipitate formed
  6. customwas isolated by filtration
  7. washwashed with water
  8. customdried at 45° C. under vacuum for 16 h

Sources & evidence

ORD record
ord-804cb165e1854961832031e5dee71638
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

Loading…