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

HRID 36504

反応式

HRID 36504 の反応式
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]

参加物

9

反応物 3

HCID 8857Ethyl Acetate2 回HCID 516920Potassium bisulfateHCID 54059189N-[2-[(Acetylthio)methyl]-3,3,3-trifluoro-1-oxopropyl]-L-leucine

生成物 1

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

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒2 回HCID 887Methanol溶媒HCID 962Water溶媒HCID 8058Hexane溶媒HCID 14923Ammonium Hydroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e9201d502a384a31b3a894e1357eef75
出典データセット
uspto-grants-1995_05
特許番号
US05414013

関連ノート

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