Hydrochloric Acid → HCID 60030580, compound

HRID 497571Notes

Reaction equation

HRID 497571 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:9][C:10]1[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])(=O)C.[Na+].O=[CH:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O>[C:27]([O:26][C:25]([NH:24][CH2:23][CH2:22][NH:3][C@@H:4]([CH2:9][C:10]1[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:31])([CH3:30])([CH3:29])[CH3:28]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 53230049Methyl (2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate dihydrochloride

Product 1

HCID 60030580HCID 60030580, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate dihydrochloride (1.06 g, 4 mmol), sodium acetate (1.3 g, 16 mmol) and 4 Å molecular sieves (500 mg) were added to a solution of tert-butyl N-(2-oxoethyl)carbamate (637 mg, 4 mmol) in methanol (10 ml), and the solution stirred for 10 minutes. Sodium cyanoborohydride (1.3 g, 16 mmol) was then added, and the reaction stirred at room temperature for 72 hours. 2M Hydrochloric acid (2 ml) and water (50 ml) were added, and the solution then basified using saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (5×100 ml), the combined organic extracts dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:diethylamine (100:0:0 to 96:2:2) to afford the title compound as a colorless oil, 220 mg, 17% yield.

Workup

  1. stirringthe reaction stirred at room temperature for 72 hours
  2. extractionThe mixture was extracted with ethyl acetate (5×100 ml)
  3. dry with materialthe combined organic extracts dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:diethylamine (100:0:0 to 96:2:2)

Sources & evidence

ORD record
ord-13626996c9ff4f3c8f3f3898a10ff49b
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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