Hydrochloric Acid → [3S,4aR,6S,8aR]-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylic Acid Dihydrochloride

HRID 1369606Notes

Reaction equation

HRID 1369606 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])C.[ClH:27]>>[ClH:27].[ClH:27].[CH2:25]([O:24][C:22]([C:20]1[N:19]=[CH:18][N:17]([CH2:16][C@H:12]2[CH2:11][CH2:10][C@@H:9]3[C@@H:14]([CH2:15][C@@H:6]([C:4]([OH:5])=[O:3])[NH:7][CH2:8]3)[CH2:13]2)[CH:21]=1)=[O:23])[CH3:26]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 9799112[3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

Product 1

HCID 69977916[3S,4aR,6S,8aR]-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylic Acid Dihydrochloride

Procedure

A solution of 0.20 g of [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (prepared in example 3) in 10 mL of 5N HCl was heated at 50° C. for three hours and then at room temperature for 18 h. The solution was evaporated and the resulting residue was chromatographed over C18 modified silica gel eluting with acetonitrile in aqueous 0.1% HCl to give 0.105 g of the title compound: MS m/z: 336 (m++1); Analysis calculated for C17H25N3O4HCl1.5H2O: C, 51.2; H, 7.35; N, 10.55. Found: C, 51.33; H, 7.04; N, 10.62.

Workup

  1. customThe solution was evaporated
  2. customthe resulting residue was chromatographed over C18 modified silica gel eluting with acetonitrile in aqueous 0.1% HCl

Sources & evidence

ORD record
ord-be98a1015afb4ebf9652bbf0bcfe5a36
Source dataset
uspto-grants-2003_06
Patent number
US06579886B2

Reaction notes

Loading…