HCID 57386047, compound → HCID 66649435, compound

HRID 420270Notes

Reaction equation

HRID 420270 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][CH:34]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([F:30])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:31])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@H:13]2[C@H:12]3[C@@H:17]([N:9]([CH2:8][C:7]4[CH:32]=[CH:33][CH:34]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=4)[C:10](=[O:31])[O:11]3)[CH2:16][S:15](=[O:18])(=[O:19])[CH2:14]2)=[CH:22][C:23]=1[F:30]

Participants

4

Reactant 1

HCID 57386047HCID 57386047, compound

Product 1

HCID 66649435HCID 66649435, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-7-(3-fluoro-4-nitro-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (4.0 g, 8.1 mmol) in THF (150 mL) was hydrogenated over 10% Pd/C (300 mg) at 45° C. and 1 bar. After 16 h the catalyst was filtered off over Celite and the filtrate was evaporated. The residue was recrystallized from THF-hexane to yield the title compound as beige crystals: TLC (hexane-EtOAc 1:1) Rf=0.29; HPLC RtA=1.94 min; ESIMS [M+NH4]+=478; 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 1H), 7.30 (d, 1H), 7.27 (s, 1H), 7.09 (d, 1H), 6.76 (dd, 1H), 6.7 (m, 2H), 4.52 (d, 1H), 4.31 (d, 1H), 3.85 (m, 1H), 3.74 (m, 1H), 3.05 (m, 3H), 2.80 (dd, 1H), 2.5-2.8 (m, 3H), 1.31 (s, 9H).

Workup

  1. filtrationAfter 16 h the catalyst was filtered off over Celite
  2. customthe filtrate was evaporated
  3. customThe residue was recrystallized from THF-hexane

Sources & evidence

ORD record
ord-5aa44a7a1a864da397d241659d054641
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

Loading…