Hydrochloric Acid → HCID 20594300, compound

HRID 1369608Notes

Reaction equation

HRID 1369608 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]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2].[ClH:32]>C(OCC)(=O)C>[ClH:32].[ClH:32].[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]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20594299HCID 20594299, compound

Product 1

HCID 20594300HCID 20594300, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

[3S,4aR,6S,8aR]-Ethyl-6-((4,5-bis-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate was dissolved in ethyl acetate (50 mL) and a solution of 1.86M hydrochloric acid in ethyl acetate (11.65 mL, 0.0217 mol) was added giving a sticky solid. The reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane (10 mL) and added dropwise to diethyl ether (150 mL) causing the precipitation of 5.09 g (47%) of [3S,4aR,6S,8aR]-Ethyl-6-((4,5-bis-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride; mp 99-101° C.

Workup

  1. customgiving a sticky solid
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  4. additionadded dropwise to diethyl ether (150 mL)
  5. customthe precipitation of 5.09 g (47%) of [3S,4aR,6S,8aR]-Ethyl-6-((4,5-bis-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate dihydrochloride

Sources & evidence

ORD record
ord-c4b5bf1c80754141bdea9f304ac7b8c6
Source dataset
uspto-grants-2003_06
Patent number
US06579886B2

Reaction notes

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