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

HRID 1625509ノート

反応式

HRID 1625509 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].O.[OH-].[Li+]>C(O)C>[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 168937Lithium hydroxide, monohydrateHCID 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 98.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To an ice-cold stirred solution of ethyl (2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylate (5.6 g, 17.8 mmol) in ethanol (18 ml) is added a solution of lithium hydroxide monohydrate (17.8 mL of 1.7 M, 30.3 mmol). The reaction mixture is stirred for 5 hours at rt. The reaction mixture is concentrated, diluted with water, washed with ether. The aqueous solution is acidified with aq. 1N HCl, extracted with CH2Cl2. The combined extracts are washed with brine, dried (Na2SO4), concentrated to afford (2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]-5-methyl-pyrrolidine-2-carboxylic acid (5 g, 94%) as a white solid.

後処理

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with water
  3. washwashed with ether
  4. extractionextracted with CH2Cl2
  5. washThe combined extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0245b5327b75455c9b3ebb6ffeed14d8
出典データセット
uspto-grants-2014_07
特許番号
US08779156B2

反応ノート

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