Hydrochloric Acid → HCID 70016797, compound

HRID 1370633Notes

Reaction equation

HRID 1370633 reaction equation
[Cl-:1].C([O:9][C:10]([CH2:12][CH2:13][CH2:14][O:15][C:16]([O:18][CH2:19][N:20]1[CH2:24][NH+:23]([CH2:25][C@@:26]([C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:48]=2[F:54])([OH:46])[C@H:27]([N:29]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][C:37]([N:40]4[CH:44]=[N:43][N:42]=[N:41]4)=[CH:36][CH:35]=3)[C:30]2=[O:45])[CH3:28])[N:22]=[CH:21]1)=[O:17])=[O:11])C1C=CC=CC=1.Cl>CO.[C].[Pd]>[Cl-:1].[F:54][C:48]1[CH:49]=[C:50]([F:53])[CH:51]=[CH:52][C:47]=1[C@:26]([OH:46])([C@H:27]([N:29]1[CH2:33][CH2:32][N:31]([C:34]2[CH:35]=[CH:36][C:37]([N:40]3[CH:44]=[N:43][N:42]=[N:41]3)=[CH:38][CH:39]=2)[C:30]1=[O:45])[CH3:28])[CH2:25][NH+:23]1[CH2:24][N:20]([CH2:19][O:18][C:16]([O:15][CH2:14][CH2:13][CH2:12][C:10]([OH:11])=[O:9])=[O:17])[CH:21]=[N:22]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69943472HCID 69943472, compound2×

Product 1

HCID 70016797HCID 70016797, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-[(3-Benzyloxycarbonylpropoxy)carbonyloxymethyl]-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium chloride (Compound 29, 155 mg) was dissolved in methanol (6 ml). To the solution were added 1N hydrochloric acid solution (0.2 ml) and 10% palladium-carbon (50% wet, 77 mg). The mixture was stirred for 0.5 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and to the filtrate was added distilled water. The mixture was concentrated under reduced pressure, and the concentrate was lyophilized 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-carboxypropoxy)carbonyloxymethyl]-1H-1,2,4-triazolium chloride (Compound 33, 122 mg) as a white powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionto the filtrate was added
  3. distillationdistilled water
  4. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-97910812d15b44a4a93ce62e853a4b62
Source dataset
uspto-grants-2003_06
Patent number
US06583164B1

Reaction notes

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