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 480365Notes

Reaction equation

HRID 480365 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[O:6]1)=[O:4].COC(C1OC(C#CCNC(OC(C)(C)C)=O)=CC=1)=O>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

5

Reactant 2

HCID 53793873Methyl 5-(3-((tert-butoxycarbonyl)amino)prop-1-yn-1-yl)furan-2-carboxylateHCID 542351595-(3-Tert-butoxycarbonylaminopropyl)-tetrahydrofuran-2-carboxylic acid methyl ester

Product 1

HCID 536486615-(3-Tert-butoxycarbonylaminopropyl)-furan-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(3-tert-Butoxycarbonylamino-propyl)-tetrahydrofuran-2-carboxylic acid methyl ester and 5-(3-tert-Butoxycarbonylamino-proDyl)-furan-2-carboxylic acid methyl ester. 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-28405d54c5e64ceb8f9ecd07b0c31478
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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