Hydrochloric Acid → HCID 178447404, compound

HRID 1590122Notes

Reaction equation

HRID 1590122 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[BH4-].[Na+].Cl>O1CCCC1.CO>[OH:2][CH2:3][CH:4]([NH:5][C:6](=[O:33])[C@H:7]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:8][C:9](=[O:25])[C@H:10]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178501418HCID 178501418, compound

Product 1

HCID 178447404HCID 178447404, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Pivaloyl-L-phenylalanyl-L phenylalanyl-L-histidine methyl ester (1.90 g) is dissolved in tetrahydrofuran (12 ml), and a solution of sodium borohydride (0.20 g) in methanol (2.5 ml) is added dropwise thereto. The mixture is stirred at room temperature for four hours, and 5% hydrochloric acid (4 ml) is added to the mixture and then the solvent is distilled off. The residue is made alkaline with an aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The extract is washed with an aqueous sodium chloride solution, dried, and concentrated to remove solvent. The residue is triturated with ethyl acetate to give 4-{2-hydroxymethyl-2-[N-(N-pivaloyl-L-phenylalanyl-L-phenylalanyl)amino]ethyl}imidazole (1.24 g) as white powder. Yield: 68.8%

Workup

  1. distillationthe solvent is distilled off
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customto remove solvent
  7. customThe residue is triturated with ethyl acetate

Sources & evidence

ORD record
ord-6148a169ed8740b7b04230e0f02b26a3
Source dataset
uspto-grants-1993_04
Patent number
US05202312

Reaction notes

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