Ethyl Acetate → N-[3,3,3-Trifluoro-2-(mercaptomethyl)-1-oxopropyl]-L-leucine

HRID 36504

반응식

HRID 36504 반응식
C([S:4][CH2:5][CH:6]([C:18]([F:21])([F:20])[F:19])[C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])(=O)C.S([O-])(O)(=O)=O.[K+].C(OCC)(=O)C>[OH-].[NH4+].O.CO.C(O)(=O)C.CCCCCC>[F:19][C:18]([F:20])([F:21])[CH:6]([CH2:5][SH:4])[C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

참가 물질

9

반응물 3

HCID 8857Ethyl Acetate2회HCID 516920Potassium bisulfateHCID 54059189N-[2-[(Acetylthio)methyl]-3,3,3-trifluoro-1-oxopropyl]-L-leucine

생성물 1

HCID 53740741N-[3,3,3-Trifluoro-2-(mercaptomethyl)-1-oxopropyl]-L-leucine

시약·촉매·용매 5

HCID 176Acetic Acid용매2회HCID 887Methanol용매HCID 962Water용매HCID 8058Hexane용매HCID 14923Ammonium Hydroxide용매

실험 절차

A suspension of the product of Example 18 (2.3 g., 6.98 mmol.) in 4.45 mL of concentrated ammonium hydroxide and 10 mL of water was stirred at room temperature under argon for 8 minutes. The resulting clear solution was acidified with 5% potassium hydrogen sulfate solution to pH 2 and extracted with 100 mL of ethyl acetate followed by 3×75 mL of additional extractions. The combined ethyl acetate extract was washed with 100 mL of brine, dried (MgSO4) and evaporated to give 1.94 g. of an off-white solid. Flash chromatography on 200 g. of silica gel eluting with ethyl acetate: hexanes:acetic acid, 100:100:1 afforded 1.72 g. of the title isomer A product as a white crystalline solid, m.p. 143°-145° C., TLC Rf =0.38 (100:50:1 ethyl acetate:hexane:acetic acid), [α]D =-62.2° (c=1.00, methanol).

후처리

  1. extractionextracted with 100 mL of ethyl acetate
  2. extractionfollowed by 3×75 mL of additional extractions
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with 100 mL of brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give 1.94 g

출처 및 근거

ORD 기록
ord-e9201d502a384a31b3a894e1357eef75
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414013

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