Methanol → 2-(5-(tert-Butoxycarbonylamino)pentyloxy)-4-fluorobenzoic acid

HRID 1019830Notes

Reaction equation

HRID 1019830 reaction equation
CO.[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])=[O:9])([CH3:6])([CH3:5])[CH3:4].O[Li].O>O>[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=1[C:19]([OH:21])=[O:20])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67448370Methyl 2-(5-(tert-butoxycarbonylamino)pentyloxy)-4-fluorobenzoate

Product 1

HCID 674481082-(5-(tert-Butoxycarbonylamino)pentyloxy)-4-fluorobenzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methanol (500 ml) and water (500 ml) were added to the crude reaction mixture obtained in Example 24. LiOH hydrate (1.4 mol) was added and the reaction mixture was stirred at room temperature for 16 h. Then, water (500 ml) was added and the organic solvent was evaporated under vacuum. The mixture was extracted with methyl tert-butyl ether to remove impurities. The water layer was adjusted to pH 8-9 and extracted again with ethyl acetate (3×500 ml). The water layer was adjusted to pH 4-5 and ethyl acetate was added. The organic layer was separated, washed with brine, dried and concentrated in vacuo. Yield: 120 g (purity 80%, 75% yield over 2 steps).

Workup

  1. customthe organic solvent was evaporated under vacuum
  2. extractionThe mixture was extracted with methyl tert-butyl ether
  3. customto remove impurities
  4. extractionextracted again with ethyl acetate (3×500 ml)
  5. additionwas added
  6. customThe organic layer was separated
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ee67415bbbd46d2a6569c61505513c7
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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