HCID 54088991, compound → HCID 53734340, compound

HRID 651666Notes

Reaction equation

HRID 651666 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=4)[CH:17]=3)(=[O:15])=[O:14])[C:8]2=[O:28])=[CH:4][C:3]=1[N+:31]([O-])=O.[H][H]>[Pd].CO.C(Cl)(Cl)Cl>[NH2:31][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:2]=1[NH2:1])[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:28]

Participants

6

Reactant 2

HCID 54088991HCID 54088991, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53734340HCID 53734340, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

10% Palladium on carbon (0.08 g) is added to a solution of 7-methoxy-naphthalene-2-sulfonic acid [1-(4-amino-3-nitrobenzyl)-2-oxopyrrolidin-3-(S)-yl]-amide (0.22 g, 0.5 mmol) (prepared as described in EXAMPLE 25, Part F) in MeOH (40 mL) and CHCl3, (3 mL) under nitrogen atmosphere. The heterogeneous mixture is hydrogenated at room temperature on a Parr apparatus under 47 p.s.i. of hydrogen for 5 hours. The catalyst is filtered and the filtrate checked by the shows no starting material. The filtrate is concentrated in vacuo and used in the subsequent step without further purification.

Workup

  1. customis hydrogenated at room temperature on a Parr apparatus under 47 p.s.i
  2. filtrationThe catalyst is filtered
  3. concentrationThe filtrate is concentrated in vacuo
  4. customused in the subsequent step without further purification

Sources & evidence

ORD record
ord-084d89d3175d44259f256dced099a4cd
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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