Methyl cis(+/-)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate → Methyl cis(+/-)-2-(acetylamino)-5-(4-amino-3-methoxypiperidin-1-yl)benzoate

HRID 43806Notes

Reaction equation

HRID 43806 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C@H:18]([NH:21]C(OCC3C=CC=CC=3)=O)[C@H:17]([O:32][CH3:33])[CH2:16]2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[H][H]>C(O)C.[C].[Pd]>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C@H:18]([NH2:21])[C@H:17]([O:32][CH3:33])[CH2:16]2)=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86648750Methyl cis(+/-)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 86648751Methyl cis(+/-)-2-(acetylamino)-5-(4-amino-3-methoxypiperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Methyl cis(±)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate obtained in Example (185c) was dissolved in ethanol (25 mL). A 10% palladium-carbon catalyst (180 mg) was added, and the mixture was stirred in a hydrogen atmosphere overnight. The reaction solution was filtered through celite and then concentrated under reduced pressure to obtain 210 mg of the title compound. The resulting compound was used for the next reaction without purification.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3fb8dc7ab42419ca6ac2a4644558142
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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