Methanesulfonyl chloride → N-Benzyloxycarbonyl-4-methanesulphonyloxy-L-cis-proline methyl ester

HRID 54623

反応式

HRID 54623 の反応式
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([O:9][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

生成物 1

HCID 53648301N-Benzyloxycarbonyl-4-methanesulphonyloxy-L-cis-proline methyl ester

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1.59 g (5.7 mmol) of N-benzyloxycarbonyl-4-hydroxy-L-cis-proline methyl ester are dissolved in 50 ml of abs. pyridine and cooled to 0° C. 0.6 ml (7.7 mmol) of methanesulphonyl chloride is added dropwise at 0° C., and the mixture is subsequently stirred at room temperature for 3 hours. The mixture is then concentrated and 100 ml of methylene chloride are added to the residue, and this latter mixture is then extracted 2 x by shaking with a 10% solution of NaHCO3, dried over sodium sulphate and concentrated once again, with the residue being subsequently distilled repeatedly with toluene. Yield: quantitative Rf : 0.33, eluent, toluene/EtOH (10:1)

後処理

  1. concentrationThe mixture is then concentrated
  2. addition100 ml of methylene chloride are added to the residue
  3. extractionthis latter mixture is then extracted 2 x
  4. stirringby shaking with a 10% solution of NaHCO3
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated once again, with the residue
  7. distillationbeing subsequently distilled repeatedly with toluene

出典と根拠

ORDレコード
ord-dab3ce6cd55e4eb5a34f6543d057f0af
出典データセット
uspto-grants-1997_04
特許番号
US05623049

関連ノート

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