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Triethylamine → (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

HRID 568266
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HRID 568266 반응식
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH:24]([OH:33])[C:25]2[N:26]3[CH:32]=[N:31][CH:30]=[C:27]3[S:28][CH:29]=2)[CH2:22][C@@H:21]([OH:34])[CH2:20]1)=[O:18])[CH:14]=[CH2:15].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH:24]([C:25]2[N:26]3[CH:32]=[N:31][CH:30]=[C:27]3[S:28][CH:29]=2)[OH:33])[CH2:22][C@@H:21]([O:34][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:20]1)=[O:18])[CH:14]=[CH2:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 516892Sodium BicarbonateHCID 70220671(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

생성물 1

HCID 86756315(3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (0.165 ml) and 0.080 ml of methanesulfonyl chloride are successively added to 313 mg of crude (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer B) in 8.5 ml of THF in an argon atmosphere at −14° C., and the mixture is stirred in this state for 40 min. Further, 0.008 ml of methanesulfonyl chloride is added thereto, and the mixture is stirred for 20 min. A 5% aqueous sodium hydrogencarbonate solution (20 ml) is added thereto, and the mixture is extracted wit 50 ml of ethyl acetate. The organic layer is dried over magnesium sulfate and filtered. The solvent is removed by evaporation under reduced pressure to give 355 mg of crude (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-(imidazo[5,1-b]thiazol-3-yl)methyl]-3-methanesulfonyloxypyrrolidine (stereoisomer B) as a slight yellow amorphous material.

후처리

  1. stirringthe mixture is stirred for 20 min
  2. extractionthe mixture is extracted wit 50 ml of ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent is removed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-97d3211958b04b05950a56b255e64a83
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06180622B2

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