Hydrochloric Acid → HCID 86758193, compound

HRID 1370631Notes

Reaction equation

HRID 1370631 reaction equation
[Cl-:1].[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C@:10]([OH:52])([C@H:33]([N:35]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43]([N:46]3[CH:50]=[N:49][N:48]=[N:47]3)=[CH:42][CH:41]=2)[C:36]1=[O:51])[CH3:34])[CH2:11][NH+:12]1[CH2:16][N:15]([CH2:17][O:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][O:25]CC2C=CC=CC=2)=[O:20])[CH:14]=[N:13]1.Cl>CO.[C].[Pd]>[Cl-:1].[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C@:10]([OH:52])([C@H:33]([N:35]1[CH2:39][CH2:38][N:37]([C:40]2[CH:41]=[CH:42][C:43]([N:46]3[CH:50]=[N:49][N:48]=[N:47]3)=[CH:44][CH:45]=2)[C:36]1=[O:51])[CH3:34])[CH2:11][NH+:12]1[CH2:16][N:15]([CH2:17][O:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][OH:25])=[O:20])[CH:14]=[N:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69943188HCID 69943188, compound2×

Product 1

HCID 86758193HCID 86758193, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-[(2R,3R)-2-(2,4-Difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[(3-benzyloxypropoxy)carbonyloxymethyl]-1H-1,2,4-triazolium chloride(Compound 25, 0.66 g) was dissolved in methanol (25 ml), and to the solution were added 1N-hydrochloric acid (0.89 ml) and 10% palladium-carbon (50% wet, 0.33 g). The mixture was stirred for 1.5 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to ODS column chromatography (eluent: methanol/water=3/2) and recrystallized from ethanol to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[(3-hydroxypropoxy)carbonyloxymethyl]-1H-1,2,4-triazolium chloride(Compound 26, 0.19 g) as colorless powdery crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-039ffbb2b872410f92a553230ce6b15b
Source dataset
uspto-grants-2003_06
Patent number
US06583164B1

Reaction notes

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