Hydrochloric Acid → HCID 20594303, compound

HRID 1369599Notes

Reaction equation

HRID 1369599 reaction equation
[CH2:1]([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[C:21]([CH3:22])=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2].[ClH:28]>C(OCC)(=O)C.C(OCC)C>[ClH:28].[ClH:28].[CH2:1]([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[C:21]([CH3:22])=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11451728HCID 11451728, compound

Product 1

HCID 20594303HCID 20594303, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.325 g of [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-5-methyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate in dry ethyl acetate (5 mL) at 20° C. was added 3.4 ml of a 1.0M solution of HCl in diethyl ether. The resulting precipitate was collected through filtration and vacuum dried at 50° C. to yield 0.214 g of the final title compound, [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-5-methyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride: MS m/z: 378.3 (m++1-HCl); 1H NMR 400 MHz (CD3OD) δ 9.12 (s, 1 H), 4.44-4.38 (m, 2H), 4.27-4.22 (m, 2H), 4.16-4.09 (m, 3H), 3.38-3.32 (t, 1 H), 3.06 (br s, 2 H), 3.08-3.02 (dd, 1H), 2.62 (s, 3H), 2.17-2.02 (m, 2H), 1.98-1.90 (m, 3H), 1.74-1.64 (m, 2H), 1.63-1.59 (m, 1H), 1.46-1.33 (m, 5H), 1.31-1.25 (t, 3H), 1.23-1.08 (m, 1H).

Workup

  1. filtrationThe resulting precipitate was collected through filtration and vacuum
  2. customdried at 50° C.

Sources & evidence

ORD record
ord-75a2d4596186427bbfb448f7098d8057
Source dataset
uspto-grants-2003_06
Patent number
US06579886B2

Reaction notes

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