1,4-Dioxane hydrochloride → HCID 178501422, compound

HRID 1590120Notes

Reaction equation

HRID 1590120 reaction equation
[CH3:1][O:2][C:3](=[O:41])[C@H:4]([CH2:35][C:36]1[N:40]=[CH:39][NH:38][CH:37]=1)[NH:5][C:6](=[O:34])[C@H:7]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:8][C:9](=[O:26])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:11]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:48]>>[ClH:48].[ClH:48].[CH3:1][O:2][C:3](=[O:41])[C@H:4]([CH2:35][C:36]1[N:40]=[CH:39][NH:38][CH:37]=1)[NH:5][C:6](=[O:34])[C@H:7]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:8][C:9](=[O:26])[C@H:10]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:11]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178501419N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester

Product 1

HCID 178501422HCID 178501422, compound

Procedure

10% Hydrogenchloride dioxane solution (30 ml) is added to N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester (2.25 g) and the mixture is stirred at room temperature for two hours. The reaction mixture is concentrated under reduced pressure to remove solvent and ether is added to the residue to give L phenylalanyl-L phenylalanyl-L-histidine methyl ester dihydrochloride (2.15 g) as white powder. The product (2.15 g) thus obtained is dissolved in dimethylformamide (15 ml), and pivaloyl chloride (0.48 g) is added thereto. Triethylamine (2.24 ml) is added dropwise to the mixture under ice-cooling and the mixture is stirred at room temperature overnight. Ethyl acetate is added to the reaction mixture and insoluble materials are filtered off. The filtrate is washed with an aqueous sodium bicarbonate solution and water, dried, and then concentrated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chroroform:methanol=12:1) and triturated with ether to give N-pivaloyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester (0.98 g). Yield ;44.8%

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove solvent and ether
  3. additionis added to the residue

Sources & evidence

ORD record
ord-3494458f56b04269b8abc2eb8b316925
Source dataset
uspto-grants-1993_04
Patent number
US05202312

Reaction notes

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