Hydrochloric Acid → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

HRID 1281199ノート

反応式

HRID 1281199 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:10]([OH:17])[CH2:11]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C(OCC)(=O)C.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:10]1[O:17][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 10904464N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methane sulfonyloxybutane

生成物 1

HCID 9813904tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

To a solution of N-tert-butoxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenyl-1-methanesulfonyloxybutane(the 2-hydroxy-1-sulfonate compound: the 1-hydroxy-2-sulfonate compound: the diol compound: the 1,2-disulfonate compund=97.1:0.1:0.4:2.3 according to the HPLC area ratio) 50 g dissolved in ethyl acetate 510 ml was added 28% sodium methylate methanol solution 58.2 g under ice-cooling and stirred for 10 min. The reaction solution was diluted with water and adjusted with 6N-HCl to pH7 to separate an organic phase, which was distilled to remove the solvent. The concentrated residue was mixed with n-heptane, stirred at the ambient temperature for 1 hr to deposit crystals, which were filtered to remove. The filtrate was washed with water to separate an organic phase, which was mixed with active charcoal 2 g, stirred at the ambient temperature for 1 hr and filtered to remove charcoal. The filtrate was cooled down to −20° C. to deposit crystals, which were filtered and dried in vacuum to obtain the N-tert-butoxycarbonyl-3(S)-amino-1,2(R)-epoxy-4-phenylbutane(98.5% according to the HPLC area ratio) 28.8 g. The diol compound and the 1,2-disulfonate compound contained in a concentration of 0.5% or less in the crystals according to the HPLC area ratio respectively.

後処理

  1. temperaturecooling
  2. customto separate an organic phase, which
  3. distillationwas distilled
  4. customto remove the solvent
  5. additionThe concentrated residue was mixed with n-heptane
  6. stirringstirred at the ambient temperature for 1 hr
  7. filtrationwere filtered
  8. customto remove
  9. washThe filtrate was washed with water
  10. customto separate an organic phase, which
  11. additionwas mixed with active charcoal 2 g
  12. stirringstirred at the ambient temperature for 1 hr
  13. filtrationfiltered
  14. customto remove charcoal
  15. filtrationwere filtered
  16. customdried in vacuum

出典と根拠

ORDレコード
ord-be5bc5a3bd274cfa84278899040f6cb8
出典データセット
uspto-grants-2002_09
特許番号
US06452026B1

反応ノート

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