Diethyl Ether → HCID 178480560, 화합물

HRID 2289044노트

반응식

HRID 2289044 반응식
[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([S:31]CC4C=CC(OC)=CC=4)[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)S(O)(=O)=O.CCOCC>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([SH:31])[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 178491728HCID 178491728, 화합물

생성물 1

HCID 178480560HCID 178480560, 화합물수율 63.7%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 7519Anisole용매

실험 절차

2.99 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylanino]pyrrolidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (1) above] were dissolved in a mixture of 21 ml of trifluoroacetic acid and 4.1 ml of anisole, and then 1.15 ml of trifluoromethanesulfonic acid were added dropwise, whilst stirring and ice-cooling, to the resulting solution. The reaction mixture was stirred for 20 minutes at room temperature, after which the mixture was poured into ether. The resulting precipitate was collected by filtration and the precipitate was dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine and dried over anhydrous sodium sulfate. The ethyl acetate solution was concentrated by evaporation under reduced pressure to obtain 1.62 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-methylpyrrolidine, in the form of an amorphous powder.

후처리

  1. temperatureice-cooling, to the resulting solution
  2. stirringThe reaction mixture was stirred for 20 minutes at room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. dissolutionthe precipitate was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate solution was concentrated by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-7fa6fb63f91544beac568ecf3fbee1fa
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090802

반응 노트

불러오는 중…