Hydrochloric Acid → (R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

HRID 2274547Notes

Reaction equation

HRID 2274547 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([N:15]1[CH:19]=[C:18]([CH2:20][C@@H:21]([NH2:25])[C:22]([OH:24])=[O:23])[N:17]=[CH:16]1)[CH:13]=[CH2:14].C(OCC)(=O)C.Cl>[OH-].[Na+]>[CH2:12]([N:15]1[CH:19]=[C:18]([CH2:20][C@@H:21]([NH:25][C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[C:22]([OH:24])=[O:23])[N:17]=[CH:16]1)[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67319867(R)-3-(1-allyl-1H-imidazol-4-yl)-2-aminopropionic acid

Product 1

HCID 67029144(R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

3.53 ml (4.24 g, 24.84 mmol) of benzyl chloroformate were added to a solution of 4.85 g (24.84 mmol) of (R)-3-(1-allyl-1H-imidazol-4-yl)-2-aminopropionic acid (as described for the (S)-enantiomer in Bioorg. Med. Chem. 2006, 14, 5981-5988) in 13 ml of 2N sodium hydroxide solution while stirring at 0° C., and stirring was continued at this temperature with addition of a further 13 ml of 2N sodium hydroxide solution for 2 h, and the mixture was them warmed to RT. The reaction mixture was covered with a layer of ethyl acetate, and the pH was adjusted to 3 to 4 with 6N hydrochloric acid. The organic phase was separated off, and the aqueous phase was washed again with ethyl acetate and then freeze dried. The residue was mixed with THF and DMF until stirrable and was thoroughly stirred, and the suspension was filtered. The resulting solution was concentrated and reacted without further purification in the next step.

Workup

  1. customThe organic phase was separated off
  2. washthe aqueous phase was washed again with ethyl acetate
  3. customfreeze dried
  4. additionThe residue was mixed with THF and DMF until stirrable and
  5. stirringwas thoroughly stirred
  6. filtrationthe suspension was filtered
  7. concentrationThe resulting solution was concentrated
  8. customreacted without further purification in the next step

Sources & evidence

ORD record
ord-39c53d822b104308877ec857026f9435
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

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