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

HRID 11852

Reaction equation

HRID 11852 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f1bdec720c284c5a909cb7ee228ab562
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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