Lithium Hydroxide → L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-

HRID 1412971ノート

反応式

HRID 1412971 の反応式
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:20]([CH3:22])[CH3:21])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([O:17]CC)=[O:16])=[O:8])=[O:4].[Li+].[OH-]>CO>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:20]([CH3:22])[CH3:21])[C:7]([N:9]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=[O:16])=[O:8])=[O:4]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67411636(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

生成物 1

HCID 67412687L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-収率 56%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(2S,5 S)-Ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate (39.3 mmol, assuming complete conversion from the previous transformation) was suspended in MeOH (200 mL) and aqueous LiOH (1.0 M, 100 mL, 100 mmol) was added. The reaction mixture was stirred o/n, then concentrated under reduced pressure to remove most of the MeOH. The aqueous solution was washed 2× with DCM before being acidified to pH˜1-2 with 10% HCl. The acidic aqueous phase was then extracted 5× with EtOAc. The combined EtOAc extracts were dried over MgSO4 filtered and concentrated under reduced pressure to afford (2S,5S)-1-((S)-2-(Methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid (6.89 g, 56% over 2 steps).

後処理

  1. concentrationthen concentrated under reduced pressure
  2. customto remove most of the MeOH
  3. washThe aqueous solution was washed 2× with DCM
  4. extractionThe acidic aqueous phase was then extracted 5× with EtOAc
  5. dry with materialThe combined EtOAc extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3580feded35f44b9899dfee3988ff9d8
出典データセット
uspto-grants-2014_12
特許番号
US08921341B2

反応ノート

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