Acetic Acid → HCID 131725058, compound

HRID 583844Notes

Reaction equation

HRID 583844 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=1)[CH3:22].C(O)(=O)C.[Na]>CCCCCC.C(OCC)(=O)C>[CH2:21]([O:23][C:24]([C:25]1[CH:26]=[C:27]([NH:31][C@H:2]2[CH2:11][CH2:10][C@@H:9]3[C@@H:4]([CH2:5][C@@H:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]3)[CH2:3]2)[CH:28]=[CH:29][CH:30]=1)=[O:32])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11400Ethyl 3-aminobenzoateHCID 5360545SodiumHCID 148779783-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 131725058HCID 131725058, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following the procedures from Example 1A, and using ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (11.4 g, 40.28 mmol), 3-aminobenzoic acid ethyl ester (3.5 g, 21.2 mmol), glacial acetic acid (5.0 mL, 84.0 mmol), and sodium triacethoxyborohydride (12.58 g, 59.36 mmol) flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 8.35 g (92% yield) of the title compound.

Sources & evidence

ORD record
ord-dd78bacfe4e14585a13ae8bcb9464390
Source dataset
uspto-grants-2005_08
Patent number
US06924294B2

Reaction notes

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