HCID 69937395, compound → HCID 69937498, compound

HRID 2281859Notes

Reaction equation

HRID 2281859 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C@@H:7]2[C@@H:10]([C:13]([F:16])([F:15])[F:14])[O:11][CH2:12][C@:6]2([C:17]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:18]=2[F:26])[N:5]=[C:4]1[NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:23][C:21]1[CH:20]=[CH:19][C:18]([F:26])=[C:17]([C@:6]23[CH2:12][O:11][C@H:10]([C:13]([F:16])([F:14])[F:15])[C@H:7]2[C:8](=[O:9])[N:3]([CH2:1][CH3:2])[C:4]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[N:5]3)[CH:22]=1

Participants

5

Reactant 2

HCID 69937395HCID 69937395, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69937498HCID 69937498, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl ((4aS,5S,7aS)-3-ethyl-7a-(2-fluoro-5-nitrophenyl)-4-oxo-5-(trifluoromethyl)-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (0.225 g, 0.46 mmol) in ethanol (30 mL) was hydrogenated over 10% Pd/C (50 mg) at RT under a balloon of hydrogen for 2 h. The catalyst was removed by filtration through Celite-washing with ethanol. The filtrate was evaporated to give the title compound (0.21 g, colourless foam). 1H NMR (400 MHz, CDCl3) δ ppm 1.14 (t, J=6.95 Hz, 3H) 1.53 (s, 9H) 3.90-4.12 (m, 3H) 4.31 (d, J=9.60 Hz, 1H) 4.45 (dd, J=9.60, 3.28 Hz, 1H) 4.47-4.56 (m, 1H) 6.46 (dd, J=6.32, 2.78 Hz, 1H) 6.63 (ddd, J=8.59, 3.79, 2.78 Hz, 1H) 6.94 (dd, J=11.12, 8.84 Hz, 1H) 10.49 (br. s., 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. washthrough Celite-washing with ethanol
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2c830c094f8c4517b61482913ccd65da
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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