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

HRID 1955019Notes

Reaction equation

HRID 1955019 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 solution 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 solution was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d4d1471fb1e45bea5ee51bba71807b5
Source dataset
uspto-grants-2000_09
Patent number
US06124314

Reaction notes

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