HCID 117857709, compound → HCID 117857548, compound

HRID 1483155Notes

Reaction equation

HRID 1483155 reaction equation
[CH:1]1([CH2:5][N:6]2[CH2:15][CH2:14][C@@:13]34[C:16]5[C:22]6[CH2:23][C@@H:7]2[C@:8]3([OH:39])[CH2:9][CH2:10][C:11](=[O:38])[C@@H:12]4[O:18][C:17]=5[C:19]([C:24]([NH:26]CC2C=CC(OC)=CC=2OC)=[O:25])=[CH:20][CH:21]=6)[CH2:4][CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[CH:1]1([CH2:5][N:6]2[CH2:15][CH2:14][C@@:13]34[C:16]5[C:22]6[CH2:23][C@@H:7]2[C@:8]3([OH:39])[CH2:9][CH2:10][C:11](=[O:38])[C@@H:12]4[O:18][C:17]=5[C:19]([C:24]([NH2:26])=[O:25])=[CH:20][CH:21]=6)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 117857709HCID 117857709, compound

Product 1

HCID 117857548HCID 117857548, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-N-(2,4-dimethoxybenzyl)-4a-hydroxy-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide (14.4 g, 27.0 mmol) in trifluoroacetic acid was stirred at ambient temperature for 2 hours. The trifluoroacetic acid was removed under reduced pressure and the residue quenched with 300 mL of ammonium hydroxide (6%). The product was extracted twice into dichloromethane (300 mL), the organic phases combined and dried (MgSO4). Filtration and removal of to the solvent under reduced pressure gave (4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-4a-hydroxy-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide (9.0 g, 87% yield); LC/MS (M+H)+=383.2.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure
  2. customthe residue quenched with 300 mL of ammonium hydroxide (6%)
  3. extractionThe product was extracted twice into dichloromethane (300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and removal of to the solvent under reduced pressure

Sources & evidence

ORD record
ord-fc31758dead94022b6af873e11834121
Source dataset
uspto-grants-2016_08
Patent number
US09416137B2

Reaction notes

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