5-(N-methyl-3-tert-butoxycarbonylaminopropyn-1-yl)-benzene-1,3-dicarboxylic acid diethyl ester → 5-(N-methyl-3-tert-butoxycarbonylaminopropyl)-benzene-1,3-dicarboxylic acid diethyl ester

HRID 1695310Notes

Reaction equation

HRID 1695310 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]#[C:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:16])[CH:9]=[C:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:7]=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:27]([O:26][C:24]([C:8]1[CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH3:16])[CH:11]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=1)=[O:25])[CH3:28]

Participants

4

Reactant 1

HCID 671454045-(N-methyl-3-tert-butoxycarbonylaminopropyn-1-yl)-benzene-1,3-dicarboxylic acid diethyl ester

Product 1

HCID 671447525-(N-methyl-3-tert-butoxycarbonylaminopropyl)-benzene-1,3-dicarboxylic acid diethyl esterYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(N-methyl-3-tert-butoxycarbonylaminopropyn-1-yl)-benzene-1,3-dicarboxylic acid diethyl ester (890 mg) in methanol (10 mL) was added palladium 10% on carbon (89 mg) and the solution was stirred at room temperature under an hydrogen atmosphere (1 bar) for 18 h. The solid was filtered off and solvent was removed in vacuo to afford 5-(N-methyl-3-tert-butoxycarbonylaminopropyl)-benzene-1,3-dicarboxylic acid diethyl ester (767 mg) as a yellow oil:

Workup

  1. filtrationThe solid was filtered off
  2. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-2cdc1d3c4a6c4d8895af4d866e5597e5
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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