Triphenylphosphine → 1-(5-tert-Butyl-isoxazol-3-yl)-3-(4-chloro-benzenesulfonyl)-3-methyl-pyrrolidin-2-one

HRID 1924862

反応式

HRID 1924862 の反応式
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([C:36]1[O:40][N:39]=[C:38]([NH:41][C:42](=[O:58])[C:43]([S:48]([C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)(=[O:50])=[O:49])([CH3:47])[CH2:44][CH2:45]O)[CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([C:36]1[O:40][N:39]=[C:38]([N:41]2[CH2:45][CH2:44][C:43]([S:48]([C:51]3[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=3)(=[O:50])=[O:49])([CH3:47])[C:42]2=[O:58])[CH:37]=1)([CH3:34])([CH3:33])[CH3:35]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58280577N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide

生成物 1

HCID 446097571-(5-tert-Butyl-isoxazol-3-yl)-3-(4-chloro-benzenesulfonyl)-3-methyl-pyrrolidin-2-one収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of diethyl azodicarboxylate (0.025 g; 0.14 mmol) in methylene chloride (1 mL) was added triphenylphosphine (0.038 g; 0.14 mmol). The mixture was stirred 20 minutes and N-(5-tert-butyl-isoxazol-3-yl)-2-(4-chlorobenzenesulfonyl)-4-hydroxy-2-methyl-butyramide (0.030 g; 0.072 mmol) in 1 mL methylene chloride was added. After 18 hours the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.024 g of product. 1H NMR (CDCl3) δ 7.83 (d, 2H), 7.55 (d, 2H), 6.73 (s, 1H), 4.03 (m, 1H), 3.95 (m, 1H), 3.25 (m, 1H), 2.29 (m, 1H), 1.52 (s, 3H), 1.35 (s, 9H). MS (ESI): m/e 397, 399 (M+H).

後処理

  1. customAfter 18 hours the volatiles were removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. customRemoval of the volatiles from the product-rich fractions

出典と根拠

ORDレコード
ord-55ff04f36fca42b3853c662356f44264
出典データセット
uspto-grants-2012_05
特許番号
US08178568B2

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