Triphenylphosphine → HCID 86722610、化合物

HRID 2271499ノート

反応式

HRID 2271499 の反応式
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:14](O)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([N:2]2[N:3]=[N:4][CH:5]=[N:1]2)[CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH:10]=[CH:11][C:12]=1[Cl:13]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594467411-Azetidinecarboxylic acid, 3-[(3,4-dichlorophenyl)hydroxymethyl]-, 1,1-dimethylethyl esterHCID 178418441HCID 178418441、化合物

生成物 1

HCID 86722610HCID 86722610、化合物収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Tetrazole (90.0 mg, 1.28 mmol) was added to tertiary butyl 3-((3,4-dichlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate (200 mg, 0.638 mmol) and triphenylphosphine (335 mg, 1.28 mmol) dissolved in the distilled tetrahydrofuran solution (15.0 mL), and diisopropyl azocarboxylate (0.25 mL, 1.28 mmol) was slowly added thereto at 0° C., and the mixture was stirred at room temperature for one day. The solvent of the reaction mixture was removed by reduced pressure evaporation to obtain a yellow liquid, which was purified by flash chromatography (n-hexane:ethyl acetate (4:1, v/v)). The product was identified as a single compound by TLC (n-hexane:ethyl acetate (4:1, v/v)) (yield: 88%, white solid). This white solid was dissolved in 10 mL of methanol solution, and 1 N HCl (3.0 mL) was added thereto, and heated to reflux at 60° C. for one day. Thereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation to obtain the title compound (KHG27280).

後処理

  1. additionwas slowly added
  2. customThe solvent of the reaction mixture was removed by reduced pressure evaporation
  3. customto obtain a yellow liquid, which
  4. customwas purified by flash chromatography (n-hexane:ethyl acetate (4:1
  5. dissolutionThis white solid was dissolved in 10 mL of methanol solution
  6. addition1 N HCl (3.0 mL) was added
  7. temperatureheated
  8. temperatureto reflux at 60° C. for one day
  9. customThereafter, the solvent of the reaction mixture was removed by reduced pressure evaporation

出典と根拠

ORDレコード
ord-8a41be24fdcf4e57a2c0c6a2848c75fe
出典データセット
uspto-grants-2015_09
特許番号
US09120771B2

反応ノート

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