Citric Acid → [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 Citrate

HRID 1369603Notes

Reaction equation

HRID 1369603 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[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])[CH3:2].[C:27]([OH:39])(=[O:38])[CH2:28][C:29]([CH2:34][C:35]([OH:37])=[O:36])([C:31]([OH:33])=[O:32])[OH:30]>CC(O)C>[C:27]([OH:39])(=[O:38])[CH2:28][C:29]([CH2:34][C:35]([OH:37])=[O:36])([C:31]([OH:33])=[O:32])[OH:30].[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[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])[CH3:2]

Participants

4

Reactant 2

HCID 311Citric 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 20594297[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 Citrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

[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 (511 mg, 1.04 mmol) was dissolved in 2-propanol (3.0 mL) and treated with a solution of citric acid (270 mg, 1.04 mmol, dissolved in 2.0 mL 2-propanol). The resulting slurry was heated to effect solution and seeded with authentic salt. The mixture was cooled slowly to room temperature with stirring and then cooled further in an ice-water bath. [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 citrate was collected by filtration as a colorless crystalline solid (717 mg, 92%).

Workup

  1. temperatureThe resulting slurry was heated
  2. temperaturecooled further in an ice-water bath
  3. filtration[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 citrate was collected by filtration as a colorless crystalline solid (717 mg, 92%)

Sources & evidence

ORD record
ord-2f37385d27ac4a3d8e46800d6f02d54e
Source dataset
uspto-grants-2003_06
Patent number
US06579886B2

Reaction notes

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