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Ammonia → 1-(3-Mercapto-1-oxopropyl)-L-proline

HRID 1252834
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HRID 1252834 반응식
C([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:19])[CH2:13][CH2:14][S:15]C(=O)C)(C)(C)C.N>>[SH:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:20])=[O:5])=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 222AmmoniaHCID 132082993-acetylthiopropanoyl-L-proline-t-butyl ester2회

생성물 1

HCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

실험 절차

The product of Step (a), 3-acetylthiopropanoyl-L-proline-t-butyl ester (0.5 g) was mixed with 4.5 ml of 5.5N methanolic ammonia at room temperature under nitrogen for one hour to remove the acetyl group. The solvent was then removed at 25° C. with a rotary evaporator. After the product was taken up in methanol and re-evaporated twice more in the rotary evaporator, the clear oily residue was dissolved in ethyl ether, washed twice with 5% potassium bisulfate and once with saturated NaCl, dried over MgSO4 and filtered. Residual solvent was removed in vacuo to yield a clear oily product, migrating as a single spot on thin layer chromatography in three separate solvent systems. The t-butyl ester protecting group was removed by reaction with trifluoroacetic acid in anisole.

후처리

  1. customto remove the acetyl group
  • customThe solvent was then removed at 25° C. with a rotary evaporator
  • customre-evaporated twice more in the rotary evaporator
  • dissolutionthe clear oily residue was dissolved in ethyl ether
  • washwashed twice with 5% potassium bisulfate and once with saturated NaCl
  • dry with materialdried over MgSO4
  • filtrationfiltered
  • customResidual solvent was removed in vacuo
  • customto yield a clear oily product
  • customseparate solvent systems
  • customThe t-butyl ester protecting group was removed by reaction with trifluoroacetic acid in anisole
  • 출처 및 근거

    ORD 기록
    ord-6de10f9b52974cbe98d26fa083fef85a
    출처 데이터셋
    uspto-grants-1988_05
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US04745124

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