tert-Butanol → 2-(Boc-amino)-4-methylthiophene

HRID 1802050

Reaction equation

HRID 1802050 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](C(O)=O)[S:5][CH:6]=1.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[CH3:34][C:35]([OH:38])([CH3:37])[CH3:36]>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:12][C:15](=[O:24])[O:38][C:35]([CH3:37])([CH3:36])[CH3:34])[S:5][CH:6]=1

Participants

5

Reactant 4

HCID 6386tert-Butanol2×HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27945844-Methylthiophene-2-carboxylic acid

Product 1

HCID 574719832-(Boc-amino)-4-methylthiophene

Procedure

A solution of 4-methyl thiophene-2-carboxylic acid (1.42 g, 10.0 mmol), triethylamine (1.50 mL, 10.8 mmol) and diphenyl phosphoryl azide (2.15 mL, 10.0 mmol) in tBuOH (20 mL) was stirred at reflux for 5 h. tBuOH was removed in vacuo. Et2O and water were added. The organic phase was washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-10% EtOAc in hexane to give tert-butyl 4-methylthiophen-2-ylcarbamate as a solid (0.880 g).

Workup

  1. customwas removed in vacuo
  2. additionEt2O and water were added
  3. washThe organic phase was washed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column, which
  7. washwas eluted with 0-10% EtOAc in hexane

Sources & evidence

ORD record
ord-b6a1908829e94859ab0233b71b884e78
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Linked notes

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