Ammonium formate → HCID 70001232, compound

HRID 1634795Notes

Reaction equation

HRID 1634795 reaction equation
C([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][CH2:22][C@H:23]([OH:40])[CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:28][CH:27]=3)[CH2:16][CH2:15]2)=[O:13])=[CH:7][CH:6]=1)C.C([O-])=O.[NH4+]>CO.[Pd]>[OH:40][C@H:23]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:28][CH:27]=1)[CH2:22][NH:21][CH2:20][CH:17]1[CH2:16][CH2:15][N:14]([C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:41])=[O:3])=[CH:6][CH:7]=2)=[O:13])[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69999017HCID 69999017, compound

Product 1

HCID 70001232HCID 70001232, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[(4-{[(2S)-2-hydroxy-3-(4-benzyloxy-phenoxy)-propylamino]-methyl}-piperidine-1-carbonyl)-amino]-benzoic acid ethyl ester (0.11 g, 0.43 mmol) and ammonium formate (0.063 g, 1 mmol) in 5 mL of methanol over 0.110 g of 10% palladium on carbon was stirred at ambient temperature overnight. The catalyst was filtered (solka floc) and the filtrate concentrated in vacuo. Trituration of the crude solid foam with Et2O provided 0.061 g of the title compound as a white solid.

Workup

  1. filtrationThe catalyst was filtered (solka floc)
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-d3a51b463ce64ed181a51d0847bfb172
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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