Imidazole → (3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one

HRID 327352ノート

反応式

HRID 327352 の反応式
[NH:1]1[CH2:4][CH2:3][C:2]1=[O:5].N1[CH:10]=[CH:9]N=C1.[CH2:11]([Si:13](Cl)([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].C(OCC)(=[O:21])C.[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>>[C:10]1([C@@H:4]2[NH:1][C:2](=[O:5])[C@@H:3]2[O:21][Si:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:11][CH3:12])[CH:9]=[CH:27][CH:26]=[CH:25][CH:29]=1

参加物

6

反応物 5

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 13819ChlorotriethylsilaneHCID 1367212-Azetidinone

生成物 1

HCID 10826417(3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one

実験手順

To azetidinone LXXI (580 mg, 3.55 mmol) in dry THF (5.0 mL) was added imidazole (265.5 mg, 3.90 mmol), followed by triethylsilyl chloride (TESCl, 0.654 mL, 3.90 mmol). The mixture was allowed to be stirred for 1 h. Ethyl acetate was added and the organic layer was washed with brine, 10% aqueous HCl and dried. Silica gel chromatography (being eluted with 25% ethyl acetate in hexane) gave 670 mg (Y: 68%) of compound LXXII as a foam.

後処理

  1. washthe organic layer was washed with brine, 10% aqueous HCl
  2. customdried
  3. washSilica gel chromatography (being eluted with 25% ethyl acetate in hexane)
  4. customgave 670 mg (Y: 68%) of compound LXXII as a foam

出典と根拠

ORDレコード
ord-f4989d7c15c64ddf8f0593550af48222
出典データセット
uspto-grants-1993_12
特許番号
US05272171

反応ノート

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