Hydrochloric Acid → HCID 53646148, compound

HRID 343320Notes

Reaction equation

HRID 343320 reaction equation
[OH-].[Na+].C([O:10][C:11](=[O:30])[C@H:12]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]#[N:29])[CH:23]=1)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1.Cl>O1CCOCC1>[C:17]([O:16][C:14]([NH:13][C@H:12]([C:11]([OH:30])=[O:10])[CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]#[N:29])[CH:23]=1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53965533HCID 53965533, compound

Product 1

HCID 53646148HCID 53646148, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1M Aqueous sodium hydroxide solution (10.8 ml, 10.8 mmol) was added dropwise over 5 minutes to a stirred, ice-cooled solution of N-t-butoxycarbonyl-3-(2-cyano-4-pyridyl)-(S)-alanine benzyl ester (Preparation 12; 2.73 g, 7.1 mmol) in 1,4-dioxan and the resulting solution allowed to warm to room temperature. After 1.5 hours, the pH of the solution was adjusted to 9 using 2M hydrochloric acid and the bulk of the organic solvent removed under reduced pressure. The residual aqueous solution was washed with ethyl acetate, acidified with solid citric acid and extracted with ethyl acetate, then the latter extracts dried (MgSO4) and evaporated under reduced pressure to furnish the title compound (1.6 g) as a white solid. Rf 0.67 (SS 13). Found: C,57.86; H,5.99; N,13.52. C14H17N3O4 requires C,57.72; H,5.88; N,14.42%.

Workup

  1. customthe bulk of the organic solvent removed under reduced pressure
  2. washThe residual aqueous solution was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialthe latter extracts dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-08682d64c6a545b9b97e58782f778fcd
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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