Hydrochloric Acid → 5-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester

HRID 2300558Notes

Reaction equation

HRID 2300558 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([C:13]#[C:14][CH2:15][NH:16]C(OCC2C=CC=CC=2)=O)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH2:14][CH2:15][NH2:16])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 545289645-(3-Benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester

Product 1

HCID 541907515-(3-Amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(3-benzyloxycarbonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid tert-butyl ester prepared of Preparation 7, Step B (1.0 g, 2.69 mmol) in 15 mL MeOH and 2.69 mL 1N HCl (aq) was added Pd(OH)2. The mixture was hydrogenated on a Parr shaker at 45 psi H2 for 16 h. The mixture was filtered through Celite®, the catalyst was replaced, and the reaction was shaken for another 6 h. The mixture was filtered through Celite® and concentrated in vacuo. The residue was chased with CCl4 and was triturated with Et2O. The product was isolated as a solid (360 mg).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationThe mixture was filtered through Celite®
  3. concentrationconcentrated in vacuo
  4. customwas triturated with Et2O

Sources & evidence

ORD record
ord-efdc6d4b38794ad994843f25e1dfcce1
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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