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

HRID 1666597노트

반응식

HRID 1666597 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ada131f5af7c4939a05a3d6d2ab721d7
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044076B2

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