Benzyl chloroformate → (S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

HRID 355524Notes

Reaction equation

HRID 355524 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].[CH3:12][N:13]1[CH:23]=[N:22][C:15]([CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])=[CH:14]1>C1COCC1.C([O-])(O)=O.[Na+]>[NH:18]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C:15]1[N:22]=[CH:23][N:13]([CH3:12])[CH:14]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 921051-Methyl-L-histidine

Product 1

HCID 13490232(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acidYield 105.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Benzyl chloroformate (0.24 mL, 1.7 mmol) was added dropwise to a slurry of 1-methyl-L-histidine (0.25 g, 1.5 mmol) in THF (5 mL) and saturated aqueous NaHCO3, (5 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated and diluted with H2O, washed with ether, and the pH adjusted to 6-7 with iN HCl. The mixture was concentrated, then diluted with CHCl3 (150 mL) and MeOH (15 mL), and stirred for 1 hour. The mixture was dried (MgSO4) and concentrated to provide 0.48 g of the title compound which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. washwashed with ether
  4. concentrationThe mixture was concentrated
  5. additiondiluted with CHCl3 (150 mL) and MeOH (15 mL)
  6. stirringstirred for 1 hour
  7. dry with materialThe mixture was dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e1458ba802774ad297b83086e0e7535f
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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