tert-Butanol → HCID 19100743, compound

HRID 1974990Notes

Reaction equation

HRID 1974990 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH3:18])=[C:12]([CH3:17])[C:13]=1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>O1CCCC1>[CH3:17][C:12]1[C:13]([NH:21][C:24]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:33])=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][C:11]=1[CH3:18]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 191008122-[[(1,1-Dimethylethoxy)carbonyl]amino]-4,5-dimethyl-3-thiophenecarboxylic acid

Product 1

HCID 19100743HCID 19100743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-t-Butoxycarbonylamino-4,5-dimethylthiophene-3-carboxylic acid (6.78 g, 25 mmol) was dissolved in 7.5 ml of tetrahydrofuran and 3.29 g (32.5 mmol) of triethylamine. Diphenylphosphoryl azide (3.29 g, 27.5 mmol) was added and the mixture stirred at room temperature whereby a heavy precipitate was formed. After 15 min., 250 ml of -t-butanol was added, and the mixture was stirred at reflux for ten days. The solvent was evaporated, the residue dissolved in methylene chloride, washed with 5% citric acid solution and saturated sodium bicarbonate, treated with charcoal and evaporated to yield 10.5 g of crude di-t-butyl 4,5-dimethylthiophene-2,3-dicarbamate as black oil, which was not further purified but processed further in the next step. 1H-NMR (CDCl6, δ): 1.5 (s, 18H), 1.9 (s, 3H) , 2.2 (s, 3H) .

Workup

  1. customwas formed
  2. stirringthe mixture was stirred
  3. temperatureat reflux for ten days
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in methylene chloride
  6. washwashed with 5% citric acid solution and saturated sodium bicarbonate
  7. additiontreated with charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-77088a6788ab465ba28fe8f24016478e
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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