Diisopropylethylamine → allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464731노트

반응식

HRID 1464731 반응식
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:26])[C:12]([S:23]([CH3:25])=O)=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([O:32][C:33]([N:35]1[CH2:39][C@@H](S)[CH2:37][C@H:36]1[CH2:41][O:42][CH2:43][CH2:44][F:45])=[O:34])[CH:30]=[CH2:31].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)C>[CH2:29]([O:32][C:33]([N:35]1[CH2:39][C@@H:25]([S:23][C:12]2[C@H:11]([CH3:26])[C@H:10]3[N:14]([C:15](=[O:16])[C@@H:9]3[C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:28])[CH3:27])[CH3:8])[C:13]=2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH2:37][C@H:36]1[CH2:41][O:42][CH2:43][CH2:44][F:45])=[O:34])[CH:30]=[CH2:31]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 57241269(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)-4-mercaptopyrrolidineHCID 86747784allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

생성물 1

HCID 57089568allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate수율 43.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of allyl (4R,5S,6S)-6-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (33 mg) and (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-mercaptopyrrolidine (21 mg) in N,N-dimethylformamide (1.0 ml) was added diisopropylethylamine (10 mg). After stirring for 2 hours at ambient temperature, the solution was diluted with diethyl ether (10 ml) and washed with water, 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine, dried, and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography [ethyl acetate-n-hexane (1:1.5, V/V)] to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (21 mg).

후처리

  1. washwashed with water, 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine
  2. customdried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography [ethyl acetate-n-hexane (1:1.5, V/V)]

출처 및 근거

ORD 기록
ord-527a11e1bcbc41588fcf0a300e563824
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306816

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