Trifluoroacetic acid → Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylate

HRID 1675559Notes

Reaction equation

HRID 1675559 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]#[C:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:8][C:9]=1[NH:10]C(OC(C)(C)C)=O)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]#[C:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:8][C:9]=1[NH2:10])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 249893453-Tert-butoxycarbonylamino-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 24989346Methyl 3-amino-5-(3,3-dimethylbut-1-yn-1-yl)thiophene-2-carboxylateYield 137.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(3,3-dimethyl-but-1-ynyl)-3-(tert-butoxycarbonyl)amino-thiophene-2-carboxylic acid methyl ester (4.344 g, 9.58 mmol) in CH2Cl2 (30 mL) is added trifluoroacetic acid (30 mL), and the mixture is stirred at room temperature overnight. Then it is evaporated to dryness, obtained residue is redissolved in CH2Cl2 and washed with aqueous NaHCO3 and brine. Organic fraction is separated, dried over Na2SO4, and concentrated to give 3.135 g of crude 5-(3,3-dimethyl-but-1-ynyl)-3-amino-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customThen it is evaporated to dryness
  2. customobtained residue
  3. washwashed with aqueous NaHCO3 and brine
  4. customOrganic fraction is separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b189d1a9b964b439d656de2fbdc4563
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Reaction notes

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