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

HRID 1625509노트

반응식

HRID 1625509 반응식
[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]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 67411636(2S,5S)-ethyl 1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylate

생성물 1

HCID 67412687L-Proline, N-(methoxycarbonyl)-L-valyl-5-methyl-, (5S)-수율 98.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0245b5327b75455c9b3ebb6ffeed14d8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779156B2

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