Sodium Thiosulfate → 4-[1-(4,5-Diamino-2-fluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 2066880Notes

Reaction equation

HRID 2066880 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([NH2:27])[C:24]([N+:28]([O-])=O)=[CH:23][C:22]=3[F:31])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.[OH-].[Na+].O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([NH2:27])[C:24]([NH2:28])=[CH:23][C:22]=3[F:31])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 24477Sodium ThiosulfateHCID 866550194-[1-(5-Amino-2-fluoro-4-nitro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 866550204-[1-(4,5-Diamino-2-fluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

60a obtained in the previous step was dissolved in acetonitrile (4 mL) and treated with Na2S2O3 (0.42 g) in 1N NaOH (4 mL). After 20 h, the mixture was poured in water and extracted with EtOAc twice. The combined extracts were dried and concentrated to afford the crude 60b.

Workup

  1. extractionextracted with EtOAc twice
  2. customThe combined extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c566be363f8d4be885d5b9aa8d73db2d
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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