3-Tert-butyl-1,2-oxazol-5-amine → N-(3-tert-Butyl-isoxazol-5-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide

HRID 1924860

反応式

HRID 1924860 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Al](C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2([CH3:31])[CH2:29][CH2:28][O:27][C:26]2=[O:30])(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:26](=[O:30])[C:25]([S:22]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=2)(=[O:24])=[O:23])([CH3:31])[CH2:29][CH2:28][OH:27])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 16682925TrimethylaluminumHCID 582805743-(4-Chloro-benzenesulfonyl)-3-methyl-dihydrofuran-2-one

生成物 1

HCID 44610058N-(3-tert-Butyl-isoxazol-5-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide収率 61.9%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

To a solution of 3-tert-butyl-isoxazol-5-ylamine (0.421 g; 3.00 mmol) in methylene chloride (5 mL) was added dropwise trimethylaluminum (1.5 mL of a 2.0 M solution in toluene; 3.00 mmol). The mixture was stirred 15 minutes and 3-(4-chloro-benzenesulfonyl)-3-methyl-dihydro-furan-2-one (0.659 g; 2.40 mmol) added. The mixture was stirred 3 hours, heated to 45° C. for approximately 40 hours, cooled to room temperature and carefully quenched with 10% aqueous citric acid, aqueous sodium tartrate and chloroform. The organic layer was dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.616 g of the desired product. 1H NMR (CDCl3) δ 9.85 (bs, 1H), 7.75 (d, 2H), 7.55 (d, 2H), 6.24 (s, 1H), 3.97 (m, 1H), 3.85 (m, 1H), 2.62 (m, 1H), 2.32 (m, 1H), 1.65 (s, 3H), 1.32 (s, 9H). MS (ESI): m/e 415, 417 (M+H).

後処理

  1. stirringThe mixture was stirred 3 hours
  2. temperaturecooled to room temperature
  3. customcarefully quenched with 10% aqueous citric acid, aqueous sodium tartrate and chloroform
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customRemoval of the volatiles in vacuo
  6. customprovided a residue which
  7. customwas purified by silica gel chromatography
  8. customRemoval of the volatiles from the product-rich fractions

出典と根拠

ORDレコード
ord-2ec5d78322c64ab181344bf71ac149d9
出典データセット
uspto-grants-2012_05
特許番号
US08178568B2

関連ノート

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