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

HRID 2290784노트

반응식

HRID 2290784 반응식
[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]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 20230261HCID 20230261, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbfd762b4eb64c0f9fa94a64c372c465
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04618617

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