Citric Acid → 1-(1,1-Dimethylethyl) (2S,4S)-4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)-1,2-pyrrolidinedicarboxylate

HRID 2185426ノート

反応式

HRID 2185426 の反応式
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C@@H:7]1[CH2:11][C@@H:10]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][N:8]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[C:24]([O:23][C:21]([N:8]1[CH2:9][C@H:10]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][C@H:7]1[C:6]([OH:28])=[O:5])=[O:22])([CH3:26])([CH3:27])[CH3:25]

参加物

7

反応物 4

HCID 311Citric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21341550N-tert-Butoxycarbonyl-trans-4-(N-tert-Butoxycarbonylaminomethyl)-L-Proline Methyl Ester

生成物 1

HCID 213415491-(1,1-Dimethylethyl) (2S,4S)-4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)-1,2-pyrrolidinedicarboxylate収率 85.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hydroxide monohydrate (29 mg) was added to a stirred solution of trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-proline methyl ester (C, 204 mg) in tetrahydrofuran (1 mL)-methanol (1 mL)-water (1 mL) at 0° C. The mixture was stirred at room temperature for 4 hr. The reaction mixture was acidified with 10% citric acid and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound (167 mg).

後処理

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-88e3fef7040a4bf29c18a18ce9218751
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

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