tert-Butanol → HCID 13580615, compound

HRID 1974958Notes

Reaction equation

HRID 1974958 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[S:11]1[CH:12]=[CH:13][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[C:10]1[NH:36][C:39]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:24]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27567723-[(tert-Butoxycarbonyl)amino]thiophene-2-carboxylic acid

Product 1

HCID 13580615HCID 13580615, compound

Procedure

A mixture of 3-t-butoxycarbonylaminothiophene-2-carboxylic acid (10.0 g, 41.1 mmol), diphenylphosphoryl azide (14.14 g, 51.37 mmol) and triethylamine (5.85 ml, 42.2 mmol) in t-butyl alcohol (1000 ml) was stirred under reflux for 10 hours. The mixture was evaporated and the residue was dissolved in methylene chloride (300 ml). The solution was washed successively with 5% aqueous citric acid, water, saturated aqueous NAHCO3, followed by evaporation to give 5.9 g of a substance which was purified by recrystallization from heptane-methylene chloride to afford di-t-butyl thiophene-2,3-dicarbamate. M.p. 168°-170° C. Litt. m.p.: 165°-167° C. (J. Chem. Res. (S), 296, 1985).

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in methylene chloride (300 ml)
  4. washThe solution was washed successively with 5% aqueous citric acid, water, saturated aqueous NAHCO3
  5. customfollowed by evaporation
  6. customto give 5.9 g of a substance which
  7. customwas purified by recrystallization from heptane-methylene chloride

Sources & evidence

ORD record
ord-12903cc9dacb4c89a8d826ef1a725ca2
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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