tert-Butanol → HCID 19100786, compound

HRID 1974977Notes

Reaction equation

HRID 1974977 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:17]([CH3:19])[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.[CH3:44][C:45]([OH:48])([CH3:47])[CH3:46]>>[CH:17]([C:12]1[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]=1)([CH3:18])[CH3:19]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100810HCID 19100810, compound

Product 1

HCID 19100786HCID 19100786, compoundYield 28%

Procedure

A mixture of 2-t-butoxycarbonylamino-4-isopropylthiophene-3-carboxylic acid (4.0 g, 14.0 mmol) in 2-methyl-2-propanol (125 ml), triethylamine (1.8 g, 18.2 mmol) and diphenylphosphoryl azide (4.25 g, 15.4 mmol) was heated at reflux for 64 h. 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 1.4 g (28%) of di-t-butyl 4-isopropylthiophene-2,3-dicarbamate. 1H-NMR (CDCl3, δ): 1.15 (d, 6H), 1.5 (s, 18H), 2.75 (m, 1H), 6.0 (br.s, 1H), 6.5 (s, 1H), 7.65 (br.s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 64 h
  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-f3d74742ab1d4f5a8bfd4e2102bc04d2
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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