Tetrahydrofuran → 3-(2-Bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

HRID 2290784ノート

反応式

HRID 2290784 の反応式
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.C(N(CC)CC)C.C1COCC1.[Br:35][CH:36]([CH3:40])[C:37](Br)=[O:38]>O>[Br:35][CH:36]([CH3:40])[C:37]([NH:1][CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1)=[O:38]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 20230261HCID 20230261、化合物

生成物 1

HCID 136909903-(2-Bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole収率 81.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 4.13 g of 3-aminomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole, 1.56 g of triethylamine and 60 ml of THF was added dropwise with stirring 3.3 g of α-bromopropionyl bromide at 0°-5° C. After stirring for 1 hour at room temperature, the reaction mixture was diluted with water and extracted with benzene. The organic phase was successively washed with sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene-ethyl acetate (5:1, v/v). Crystallization of the clean fractions from diisopropyl ether yielded 4.88 g of 3-(2-bromopropionylaminomethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as colorless needles, m.p. 98°-99° C.

後処理

  1. additionwas added dropwise
  2. extractionextracted with benzene
  3. washThe organic phase was successively washed with sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed over silica gel
  7. customCrystallization of the clean fractions from diisopropyl ether

出典と根拠

ORDレコード
ord-dbfd762b4eb64c0f9fa94a64c372c465
出典データセット
uspto-grants-1986_10
特許番号
US04618617

反応ノート

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