Methyl N-(triethylammoniosulfonyl)carbamate → 2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole

HRID 1666597ノート

反応式

HRID 1666597 の反応式
[CH:1]([O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([NH:11][NH:12][C:13](=O)[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:16]([CH2:29][CH3:30])[CH:15]=2)=[O:10])=[CH:7][C:6]=1[CH3:34])([CH3:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.C(OCC)C>[CH2:22]([O:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([C:13]2[O:10][C:9]([C:8]3[CH:32]=[CH:33][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH3:34])[CH:7]=3)=[N:11][N:12]=2)=[CH:15][C:16]=1[CH2:29][CH3:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

5

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 674440334-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide

生成物 1

HCID 674468842-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole収率 83.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide (1.57 g, 3.40 mmol) and Burgess reagent (1.06 g, 4.43 mmol) in THF (30 mL) is heated to 110° C. under microwave irradiation for 3 min. The mixture is cooled, diluted with diethyl ether, washed with water, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole (1.25 g) as a colourless oil; LC-MS: tR=1.24 min, [M+1]+=443.58.

後処理

  1. temperatureThe mixture is cooled
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 5:1

出典と根拠

ORDレコード
ord-ada131f5af7c4939a05a3d6d2ab721d7
出典データセット
uspto-grants-2011_10
特許番号
US08044076B2

反応ノート

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