Hydrochloric Acid → HCID 178501398, compound

HRID 497556Notes

Reaction equation

HRID 497556 reaction equation
[NH:1]1[CH2:5][CH:4]([CH2:6][C@H:7]([NH:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])[NH:3][CH2:2]1.O=[CH:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].Cl.C(=O)([O-])O.[Na+]>CO>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][N:12]([CH3:13])[C@@H:7]([CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 86586083HCID 86586083, compound

Product 1

HCID 178501398HCID 178501398, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2S)-3-(4-imidazolidinyl)-2-(methylamino)propanoate (1 g, 4.55 mmol), of tert-butyl N-(2-oxoethyl)carbamate (833 mg, 5.23 mmol), sodium acetate (1.494 g, 18.22 mmol) and sodium cyanoborohydride (572 mg, 9.10 mmol) in methanol (30 ml) was stirred at 0° C. under a nitrogen atmosphere. The mixture was allowed to warm to room temperature then aqueous hydrochloric acid (5 ml, 1N) was added, followed by saturated aqueous sodium hydrogen carbonate solution. The solution was filtered and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol (100:5), to afford the title compound, 900 mg, 61% yield.

Workup

  1. filtrationThe solution was filtered
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with dichloromethane:methanol (100:5)

Sources & evidence

ORD record
ord-9e7fca384a0c42d980612e869db29f50
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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