tert-Butanol → HCID 19100702, compound

HRID 1974992Notes

Reaction equation

HRID 1974992 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([CH3:19])=[C:12]([CH2:17][CH3:18])[C:13]=1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>O1CCCC1>[CH2:17]([C:12]1[C:13]([NH:22][C:25]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:34])=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][C:11]=1[CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100687HCID 19100687, compound

Product 1

HCID 19100702HCID 19100702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-t-Butoxycarbonylamino-4-ethyl-5-methylthiophene-3-carboxylic acid (34.2 g, 0.12 mol) was dissolved in 35 ml of tetrahydrofuran and 15.8 ml (21.6 g, 0.156 mol) of triethylamine, and diphenylphosphoryl azide (36.3 g, 0.132 mol) was added, whereby the temperature rose to 47° C. After 30 min at room temperature, 1200 ml of t-butanol was added, and the mixture was refluxed for seven days. The dark mixture was evaporated, dissolved in methylene chloride, washed with 54 citric acid, saturated sodium bicarbonate, treated with charcoal and evaporated to yield 55.8 g of a dark oil of crude di-t-butyl 4-ethyl-5-methylthiophene-2,3-dicarbamate which was not further purified.

Workup

  1. customrose to 47° C
  2. temperaturethe mixture was refluxed for seven days
  3. customThe dark mixture was evaporated
  4. dissolutiondissolved in methylene chloride
  5. washwashed with 54 citric acid, saturated sodium bicarbonate
  6. additiontreated with charcoal
  7. customevaporated

Sources & evidence

ORD record
ord-727102f849734547ad3567ef508bd34f
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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