Hydrochloric Acid → Methyl 5-(3-aminopropyl)thiophene-2-carboxylate

HRID 2298208Notes

Reaction equation

HRID 2298208 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

HCID 313Hydrochloric AcidHCID 541388975-(3-tert-Butoxycarbonylamino-propyl)-thiophene-2-carboxylic Acid Methyl Ester

Product 1

HCID 19989043Methyl 5-(3-aminopropyl)thiophene-2-carboxylateYield 400.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(3-tert-butoxycarbonylamino-propyl)-thiophene-2-carboxylic Acid methyl ester (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 organic layer was 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

  1. concentrationThe solution was concentrated to a solid which
  2. customwas partitioned between EtOAc and saturated NaHCO3
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8a35fe462c54915b17b6242090ef828
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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