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Hydrochloric Acid → (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568265
ノート
印刷プレビュー

反応式

HRID 568265 の反応式
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([O:23][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([OH:23])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20639577HCID 20639577、化合物

生成物 1

HCID 70220671(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine収率 113.9%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

Concentrated hydrochloric acid (0.34 ml) is added dropwise to a solution of 372 mg of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer B), described in Synthesis Example 4-a), in 8.5 ml of dry acetonitrile under ice cooling (internal temperature 3° C.). The mixture is stirred in this state for 20 min and diluted with 50 ml of ethyl acetate, and the diluted solution is adjusted to pH 9.2 by addition of a 5% aqueous sodium hydrogencarbonate solution, followed by shaking. The organic layer is separated. The aqueous layer is extracted twice with 50 ml of ethyl acetate while adjusting the pH value to 9.2 by addition of a 5% aqueous sodium hydrogencarbonate solution. The organic layer is combined with the above organic layer, and the combined organic layers are dried over magnesium sulfate, followed by filtration and the removal of the solvent by evaporation under reduced pressure to give 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) as a slight yellow viscous material.

後処理

  1. stirringby shaking
  2. customThe organic layer is separated
  3. extractionThe aqueous layer is extracted twice with 50 ml of ethyl acetate
  4. additionby addition of a 5% aqueous sodium hydrogencarbonate solution
  5. dry with materialthe combined organic layers are dried over magnesium sulfate
  6. filtrationfollowed by filtration
  7. customthe removal of the solvent
  8. customby evaporation under reduced pressure

出典と根拠

ORDレコード
ord-fd9afb23ef1e49e7a3a407b1f047bc06
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06180622B2

反応ノート

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