M-Cresol → Nalpha-(5-(N-2-picolylaminomethyl)thiophene-2-carbonyl)-L-ornithine

HRID 11852

反応式

HRID 11852 の反応式
FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.C1C(O)=CC=CC=1C.C([N:31]([CH2:39][C:40]1[S:44][C:43]([C:45]([NH:47][C@H:48]([C:63]([OH:65])=[O:64])[CH2:49][CH2:50][CH2:51][NH:52]C(OCC2C=CC=CC=2)=O)=[O:46])=[CH:42][CH:41]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)(OC(C)(C)C)=O>>[N:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][CH2:39][C:40]1[S:44][C:43]([C:45]([NH:47][C@H:48]([C:63]([OH:65])=[O:64])[CH2:49][CH2:50][CH2:51][NH2:52])=[O:46])=[CH:42][CH:41]=1

参加物

5

反応物 4

HCID 342M-CresolHCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 86592265Nalpha-(5-(N-Boc-N-2-picolylaminomethyl)thiophene-2-carbonyl)-Ndelta-Cbz-L-ornithine

生成物 1

HCID 86592264Nalpha-(5-(N-2-picolylaminomethyl)thiophene-2-carbonyl)-L-ornithine収率 53.3%

実験手順

A mixed solution of trifluoroacetic acid (1.4 ml), thioanisole (0.36 ml), and m-cresol (0.32 ml) was added to the compound obtained in Example 14-3 (56.2 mg). After 1.5 hours, the reaction solution was concentrated. Methanol was added to the residue and the mixture was washed with hexane. The methanol layer was concentrated and the residue was crude-purified by silica gel column chromatography (3 g, chloroform/methanol/water=7/3/0.5) to obtain the title compound (18.2 mg) as colorless syrup.

後処理

  1. concentrationthe reaction solution was concentrated
  2. additionMethanol was added to the residue
  3. washthe mixture was washed with hexane
  4. concentrationThe methanol layer was concentrated
  5. customthe residue was crude-purified by silica gel column chromatography (3 g, chloroform/methanol/water=7/3/0.5)

出典と根拠

ORDレコード
ord-f1bdec720c284c5a909cb7ee228ab562
出典データセット
uspto-grants-2006_08
特許番号
US07098215B2

関連ノート

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