Acetic Acid → (2S)-2-(5-(N-2-picolylaminomethyl)thiophene-2-carbonylamino)-5-(5,6,7,8-tetrahydroquinolin-8-ylamino)valeric Acid

HRID 11853Notes

Reaction equation

HRID 11853 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[S:14][C:13]([C:15]([NH:17][C@H:18]([C:23]([OH:25])=[O:24])[CH2:19][CH2:20][CH2:21][NH2:22])=[O:16])=[CH:12][CH:11]=1.C(O)(=O)C.[N:30]1[C:39]2[C:38](=O)[CH2:37][CH2:36][CH2:35][C:34]=2[CH:33]=[CH:32][CH:31]=1.C([BH3-])#N.[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][C:10]1[S:14][C:13]([C:15]([NH:17][C@@H:18]([CH2:19][CH2:20][CH2:21][NH:22][CH:38]2[C:39]3[N:30]=[CH:31][CH:32]=[CH:33][C:34]=3[CH2:35][CH2:36][CH2:37]2)[C:23]([OH:25])=[O:24])=[O:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 86592264Nalpha-(5-(N-2-picolylaminomethyl)thiophene-2-carbonyl)-L-ornithine

Product 1

HCID 69638609(2S)-2-(5-(N-2-picolylaminomethyl)thiophene-2-carbonylamino)-5-(5,6,7,8-tetrahydroquinolin-8-ylamino)valeric AcidYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 14-4 (18.2 mg) was dissolved in methanol (0.6 ml), and acetic acid (0.06 ml), 5,6,7,8-tetrahydroquinolin-8-one (16 mg), and sodium cyanoborohydride (7 mg) were added. After 3 days, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (1 g, chloroform/methanol=5/1). 1 mol/l hydrochloric acid was added to the resulting colorless syrup, and the mixture was concentrated and dried under reduced pressure to obtain ahydrochloride of the title compound (6.7 mg) as a white solid.

Workup

  1. concentrationthe reaction solution was concentrated
  2. customThe residue was purified by silica gel column chromatography (1 g, chloroform/methanol=5/1)
  3. addition1 mol/l hydrochloric acid was added to the resulting colorless syrup
  4. concentrationthe mixture was concentrated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-e7479874898141028e1d5a7be0f6d12d
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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