tert-Butanol → HCID 19100786、化合物

HRID 1974977ノート

反応式

HRID 1974977 の反応式
[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]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100810HCID 19100810、化合物

生成物 1

HCID 19100786HCID 19100786、化合物収率 28%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f3d74742ab1d4f5a8bfd4e2102bc04d2
出典データセット
uspto-grants-1994_02
特許番号
US05284847

反応ノート

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