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

反応式

HRID 11848 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a446da7f8266422f9bd324e68e376165
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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