HCID 86726800, compound → HCID 86726801, compound

HRID 1499576Notes

Reaction equation

HRID 1499576 reaction equation
[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([N+:31]([O-])=O)[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[C:17]([OH:22])([CH3:21])[C@H:16]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]>C(O)(=O)C.CCOC(C)=O.[Fe]>[C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:31])[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[C:17]([OH:22])([CH3:21])[C@H:16]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 86726800HCID 86726800, compound

Product 1

HCID 86726801HCID 86726801, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{(3R,5S)-3-[(tert-Butoxycarbonyl)amino]-4-hydroxy-4,5-dimethylpiperidin-1-yl}-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (198 mg, 0.426 mmol) was dissolved in acetic acid (2.8 mL), and iron powder (0.36 g, 6.4 mmol) was added to the solution. Reaction was stirred at room temperature for 2 h. The mixture was diluted with 30 mL of EtOAc, filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in EtOAc, and neutralized with NaHCO3. The layers were separated, and the aqueous layer was extracted with further EtOAc. The combined organic layers were dried and concentrated under reduced pressure to give the sub-title compound as a white solid (176 mg, 95%), which was used in the next step without further purification. LCMS calc. for C22H35N4O5 (M+H)+ m/z=435.3. found 435.1.

Workup

  1. customReaction
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe resulting residue was dissolved in EtOAc
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with further EtOAc
  7. customThe combined organic layers were dried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-526c9bdfbabd40ffa15b4b6801eda35d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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