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1,2-Dichloroethane → tert-Butyl 5-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)isoindoline-2-carboxylate

HRID 710469
ノート
印刷プレビュー

反応式

HRID 710469 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].O[NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23]2)=[NH:19].C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:17]=[C:18]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23]4)[N:19]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 794173,4-Diethoxybenzoic acidHCID 178451481HCID 178451481、化合物

生成物 1

HCID 86661809tert-Butyl 5-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)isoindoline-2-carboxylate収率 20.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A mixture of 3,4-diethoxybenzoic acid (0.19 g; 0.904 mmol), a product of Step D (0.25 g; 0.904 mmol) and EDC (0.27 g; 1.4 mmol) in anhydrous DMF (2 ml) was stirred at ˜60° C. for 1 h, then cooled to room temperature and diluted to 20 ml with EtOAc. This was washed with H2O (2×5 ml), brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was diluted to 3 ml with anhydrous diglyme and 1M TBAF in THF (0.5 ml) was added and the resulting mixture was stirred at ˜80° C. for 1 h, then solvents were removed in vacuo. The residue was purified by crystallization from MeOH, to give the title compound (0.084 g; 20%) as greyish solid. 1H-NMR (CDCl3) 1.4-1.6 (m, 15H+H2O); 4.14-4.24 (m, 4H); 4.7-4.76 (m, 4H); 6.97 (d, 1H, J=6 Hz); 7.32-7.4 (m, 1H); 7.66 (d, 1H, J=3 Hz); 7.78 (dd, 1H, J=3, 9 Hz); 8.02-8.08 (m, 2H).

後処理

  1. washThis was washed with H2O (2×5 ml), brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customfiltrate evaporated to dryness
  5. additionThe residue was diluted to 3 ml with anhydrous diglyme and 1M TBAF in THF (0.5 ml)
  6. additionwas added
  7. customsolvents were removed in vacuo
  8. customThe residue was purified by crystallization from MeOH

出典と根拠

ORDレコード
ord-f98aa3ddcb494a7eb53b3bb55670ee16
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

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