tert-Butanol → HCID 19100786, 화합물

HRID 1974977노트

반응식

HRID 1974977 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 19100786HCID 19100786, 화합물수율 28%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f3d74742ab1d4f5a8bfd4e2102bc04d2
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05284847

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