Hydrochloric Acid → HCID 69820402, compound

HRID 1840523Notes

Reaction equation

HRID 1840523 reaction equation
[OH-].[Li+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([O:16]C)=[O:15])=[N:8][CH:9]=1.Cl>CO.O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([OH:16])=[O:15])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86590135HCID 86590135, compound

Product 1

HCID 69820402HCID 69820402, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (1.2 g, 28.6 mmol) is added, at 0° C., to a solution of methyl (S)-5-(5-amino-2-pyrazinyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pentanoate (7.75 g, 23.9 mmol) in methanol (60 ml) and water (20 ml). The mixture is allowed to warm to room temperature and stirring is continued for 18 hours. The methanol is evaporated off under reduced pressure and the residue obtained is cooled to 0° C., acidified to pH 3-4 with 1N hydrochloric acid (30 ml), extracted with ethyl acetate (2×200 ml), washed with brine (50 ml), dried over sodium sulphate, filtered and concentrated under reduced pressure. 7.17 g of (S)-5-(5-amino-2-pyrazinyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pentanoic acid are obtained in the form of a white powder, which is used without further purification in the following step.

Workup

  1. customThe methanol is evaporated off under reduced pressure
  2. customthe residue obtained
  3. temperatureis cooled to 0° C.
  4. extractionextracted with ethyl acetate (2×200 ml)
  5. washwashed with brine (50 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03d9dab340a740b1b7054d10f7dba114
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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