Sodium cyanoborohydride → (2S)-2-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)amino-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric Acid

HRID 11848

Reaction equation

HRID 11848 reaction equation
[C:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][C@H:26]([C:41]([OH:43])=[O:42])[CH2:27][CH2:28][CH2:29][NH:30]C(OCC2C=CC=CC=2)=O)=[O:24])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:44]1[C:53]2[C:52](=O)[CH2:51][CH2:50][CH2:49][C:48]=2[CH:47]=[CH:46][CH:45]=1.C([BH3-])#N.[Na+]>O1CCOCC1.O.CO.C(O)(=O)C.[Pd]>[C:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][C@@H:26]([CH2:27][CH2:28][CH2:29][NH:30][CH:52]2[C:53]3[N:44]=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:49][CH2:50][CH2:51]2)[C:41]([OH:43])=[O:42])=[O:24])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

8

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 86592262Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithine

Product 1

HCID 21043726(2S)-2-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)amino-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric AcidYield 20.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

The compound obtained in Example 12-4 (149.9 mg) was dissolved in a dioxane/water (8/2) solution (7.5 ml). After the addition of 10% Pd—C (154.6 mg), the mixture was stirred for 4.5 hours under hydrogen atmosphere at room temperature. After the reaction, the catalyst was removed by filtration through celite and the solvent was removed by distillation under reduced pressure to obtain a crude product (100.2 mg). 75.4 mg of the crude product was dissolved in methanol (1.5 ml). Then, 5,6,7,8-tetrahydroquinolin-8-one (53.6 mg) and sodium cyanoborohydride (43.2 mg) were added. 25 drops of acetic acid was added to adjust the pH of the mixture to about 5. The mixture was stirred for 22 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1) to obtain the title compound (30.6 mg) as white foam.

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration through celite
  3. customthe solvent was removed by distillation under reduced pressure
  4. customto obtain a crude product (100.2 mg)
  5. stirringThe mixture was stirred for 22 hours at room temperature
  6. customAfter the reaction
  7. customthe solvent was removed by distillation
  8. customThe residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-a446da7f8266422f9bd324e68e376165
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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