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

HRID 2290784Notes

Reaction equation

HRID 2290784 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dbfd762b4eb64c0f9fa94a64c372c465
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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