Hydrochloric Acid → HCID 21927819, compound

HRID 585574Notes

Reaction equation

HRID 585574 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>O.CO>[C:3]([O:7][C:8]([N:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21927828HCID 21927828, compound

Product 1

HCID 21927819HCID 21927819, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

NaOH (240 mg, 6 mmol) was dissolved in water (3 mL) and MeOH (10 mL). This solution was added to methyl 5-[(tert-butoxycarbonyl)(pyridin-2-yl)amino]pentanoate (200 mg, 0.64 mmol) dissolved in MeOH (15 mL). The mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 2N HCl to pH 7. The solvent was removed under reduced pressure. A citric acid solution (10 mL) was added and the mixture was extracted with ethyl acetate, dried (MgSO4) and concentrated to give 128 mg (68%) of the product. 1H NMR (CDCl3) 8.36-8.34 (m, 1H), 7.65-7.52 (m, 2H), 7.02-6.98 (m, 1H), 3.97-3.91 (m, 2H), 2.38-2.32 (m, 2H), 1.69-1.62 (m, 4H), 1.50 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionA citric acid solution (10 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f7d306e4acb4131bd7b3c67e16e6d7b
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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