Hydrochloric Acid → Methyl 5-(3-aminopropyl)thiophene-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13]C(OC(C)(C)C)=O)=[CH:8][CH:9]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:9]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 5-(3-tert-butoxycarbonylamino-propyl)-thiophene-2-carboxylic acid methyl ester prepared of Preparation 5, Step B (0.118 g, 0.5 mmol) in 50 mL MeOH was cooled to 0° C. and was saturated with HCl (g). The reaction was stirred at room temperature for 90 minutes. The solution was concentrated to a solid which was partitioned between EtOAc and saturated NaHCO3. The layers were separated, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an oil (399 mg). MS 200 (M+1).
Workup
- concentrationThe solution was concentrated to a solid which
- customwas partitioned between EtOAc and saturated NaHCO3
- customThe layers were separated
- washthe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-83c9bc8b9b7a4cf5af2a792aacf5c23f
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442702B2
Reaction notes
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