Acetic Acid → HCID 57054788, 화합물

HRID 1078719노트

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HRID 1078719 반응식
C[O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[Cl-].[Li+].[BH4-].[Na+].[C:26](O)(=[O:28])C>O1CCCC1CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([N:5]1[CH2:6][C@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:8][C@:4]1([CH2:26][OH:28])[C:3]([OH:2])=[O:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 57054788HCID 57054788, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 7360Tetrahydrofurfuryl alcohol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-methanesulfonyloxyproline methyl ester (10.0 g, 30.9 mmol) in tetrahydrofuran--methanol (1:1, 100 ml) were successively added lithium chloride (3.93 g, 92.8 mmol) and sodium borohydride (3.51 g, 92.8 mmol). The reaction solution was stirred at room temperature for 11 h. Acetic acid (2 ml) was added to the reaction solution, and ethyl acetate and water were added thereto. The mixture was concentrated in vacuo. The residue was dissolved in water and ethyl acetate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain a residue of (2S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxyproline (9.41 g).

후처리

  1. additionwere added
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionethyl acetate and extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-9853c9091ad24a42995e6ad36451466c
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05550121

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