tert-Butanol → HCID 19100804, compound

HRID 1974980Notes

Reaction equation

HRID 1974980 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:17]2[CH2:19][CH2:18]2)[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.[CH3:44][C:45]([OH:48])([CH3:47])[CH3:46]>>[CH:17]1([C:12]2[C:13]([NH:22][C:25]([O:48][C:45]([CH3:47])([CH3:46])[CH3:44])=[O:34])=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][CH:11]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100820HCID 19100820, compound

Product 1

HCID 19100804HCID 19100804, compoundYield 52%

Procedure

A mixture of 2-t-butoxycarbonylamino-4-cyclopropylthiophene-3-carboxylic acid (2.6 g, 9.1 mmol) in 2-methyl-2-propanol (100 ml), triethylamine (1.2 g, 11.9 mmol) and diphenylphosphoryl azide (2.8 g 10.1 mmol) was heated at reflux for 84h. The reaction mixture was concentrated in vacuo and the residue taken up in dichloromethane which was successively washed with a 5% citric acid solution, water and an aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and concentrated in vacuo to give 1.7 g (52%) of di-t-butyl 4-cyclopropylthiophene-2,3-dicarbamate. 1H-NMR (CDCl3, δ) : 0.55 (m, 2H) , 0.85 (m, 2H), 1.52 (s, 9H), 1.55 (s, 9H), 1.60 (s, 1H), 6.3 (br.s, 1H), 6.35 (s, 1H), 8.15 (br.s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 84h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washwas successively washed with a 5% citric acid solution, water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-307934ca205942fa92592b1be60d6ef0
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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