Sodium Hydroxide → HCID 86726826, compound

HRID 1499608Notes

Reaction equation

HRID 1499608 reaction equation
[CH:1]1([C@H:4]2[CH2:9][N:8]([C:10]3[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]4[CH2:19][CH2:20][CH2:21][C:11]=34)[CH2:7][C@@H:6]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C@@H:5]2[OH:30])[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH:1]1([C@H:4]2[CH2:9][N:8]([C:10]3[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N+:13]([O-:39])=[C:12]4[CH2:19][CH2:20][CH2:21][C:11]=34)[CH2:7][C@@H:6]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[C@@H:5]2[OH:30])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86726825HCID 86726825, compound

Product 1

HCID 86726826HCID 86726826, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl [(3R,4R,5S)-5-cyclopropyl-4-hydroxy-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (0.113 g, 0.270 mmol) in anhydrous DCM (2.5 mL) was cooled to 0° C. and mCPBA (0.080 g, 0.33 mmol, 4×0.020 g) was added portion-wise. After 15 min., the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. The reaction was quenched by the addition of a solution of Na2S2O3 (0.051 g, 0.32 mmol) in water (1 mL) followed by 4 M aq. NaOH (1 mL). The layers were separated and the organic fraction was concentrated and purified by flash column chromatography (20 g silica gel column, eluting with 0-30% MeOH/EtOAc) to afford the sub-title compound (0.050 g, 43%). LCMS (ESI) m/z calc. for C21H31N4O6 435.2 [M+H]+. found 435.0.

Workup

  1. customThe layers were separated
  2. concentrationthe organic fraction was concentrated
  3. custompurified by flash column chromatography (20 g silica gel column, eluting with 0-30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-a4fe56759fca41ed9a8c851ec0a3db99
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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