Methyl 5-(3-((tert-butoxycarbonyl)amino)prop-1-yn-1-yl)furan-2-carboxylate → 5-(3-Tert-butoxycarbonylaminopropyl)-furan-2-carboxylic acid methyl ester

HRID 1699091Notes

Reaction equation

HRID 1699091 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:10]#[C:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:9]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 53793873Methyl 5-(3-((tert-butoxycarbonyl)amino)prop-1-yn-1-yl)furan-2-carboxylate

Product 1

HCID 536486615-(3-Tert-butoxycarbonylaminopropyl)-furan-2-carboxylic acid methyl esterYield 24.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(3-tert-butoxycarbonylamino-prop-1-ynyl)-furan-2-carboxylic acid methyl ester (1.69 g) in MeOH (50 mL) was added 10% palladium on carbon (850 mg) and the mixture was hydrogenated on a Parr shaker at 50 psi for 18 h. The catalyst was removed via filtration through Celite and the volatiles were concentrated in vacuo. Flash chromatography (hexanes:EtOAc 4:1) provided 5-(3-tert-butoxycarbonylamino-propyl)-furan-2-carboxylic acid methyl ester (422 mg, MS 284 M+) followed by 5-(3-tert-butoxycarbonylamino-propyl)-tetrahydrofuran-2-carboxylic acid methyl ester (903 mg).

Workup

  1. customThe catalyst was removed via filtration through Celite
  2. concentrationthe volatiles were concentrated in vacuo

Sources & evidence

ORD record
ord-d69b9c80677144fea8b0cf81487e9fce
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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