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

HRID 1924862

반응식

HRID 1924862 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-55ff04f36fca42b3853c662356f44264
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178568B2

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