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 480344

Reaction equation

HRID 480344 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-54e3f08aeafa45a0842c63d170c15dc3
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Linked notes

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