Sodium hydride → methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate

HRID 927921Notes

Reaction equation

HRID 927921 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[C:16]([C@H:17]2[CH2:21][CH2:20][O:19][C@H:18]2[CH2:22]OS(C)(=O)=O)=[CH:15][CH:14]=[C:13]([NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=[O:5])[CH3:4].[Cl-].[NH4+]>C1COCC1>[C:3]([N:6]1[C:7]2[C:16](=[CH:15][CH:14]=[C:13]([NH:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:31])[CH3:32])[C:8]=2[C:9]([O:11][CH3:12])=[O:10])[C@H:17]2[CH2:21][CH2:20][O:19][C@H:18]2[CH2:22]1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86713287methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(methanesulfonyl-oxymethyl)tetrahydrofuran-3-yl]benzoate2×

Product 1

HCID 86713286methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylateYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.02 g) was added to a solution of methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(methanesulfonyl-oxymethyl)tetrahydrofuran-3-yl]benzoate (Intermediate 31, 0.166 g) in THF (3 mL) and the mixture was stirred at room temperature for 20 minutes. A saturated aqueous solution of ammonium chloride was added and the mixture was extracted with DCM, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (0.15 g) as a tan coloured solid.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-0b2ef623dcd84fb6abe4cbb73b00c5f5
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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