Hydrochloric Acid → 6-(Di-pyridin-2-yl-amino)-hexanoic acid

HRID 523891

Reaction equation

HRID 523891 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl.CCOC(C)=O>O.C1COCC1>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:24])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 585450216-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

Product 1

HCID 585450356-(Di-pyridin-2-yl-amino)-hexanoic acidYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (12 mg, 0.50 mmol) in water (0.3 mL) was added to II (33 mg, 0.11 mmol) in THF (0.8 mL) at rt. After 2 h, the reaction mixture was neutralized with 2N HCl, and was then poured onto brine (5 mL), and EtOAc (5 mL) was added. The phases were separated and the aqueous phase was extracted with EtOAc (2×2 mL). The organic phases were combined, dried over MgSO4, filtered, and then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:1 to 100:4) as eluant to furnish III as a colourless oil (18.1 mg, 58%).

Workup

  1. additionwas added
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×2 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c6ba30c29e64dfaaf88192370500a23
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Linked notes

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