5-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic Acid Methyl Ester → 5-(3-tert-Butoxycarbonylamino-propyl)-thiophene-2-carboxylic Acid Methyl Ester

HRID 1595900Notes

Reaction equation

HRID 1595900 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S: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]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1[S: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 540753395-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic Acid Methyl Ester

Product 1

HCID 541388975-(3-tert-Butoxycarbonylamino-propyl)-thiophene-2-carboxylic Acid Methyl EsterYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(3-tert-butoxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester (2.06 g) and 10% palladium on carbon (1.03 g) in 50 mL MeOH was hydrogenated on a Parr shaker at 50 psi H2 for 16 h. The reaction was filtered through Celite with the aid of MeOH and the filtrate was concentrated in vacuo to afford the title compound as a solid (1.93 g). MS 317 (M+18).

Workup

  1. filtrationThe reaction was filtered through Celite with the aid of MeOH
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4e233b84b508483e80b7987e65a040de
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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