1-Hydroxybenzotriazole → Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithine

HRID 11847

反応式

HRID 11847 の反応式
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:42]([N:49]([CH2:57][C:58]1[CH:66]=[CH:65][C:61]([C:62](O)=[O:63])=[CH:60][N:59]=1)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>CN(C=O)C>[C:42]([N:49]([CH2:57][C:58]1[CH:66]=[CH:65][C:61]([C:62]([NH:16][C@H:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[O:63])=[CH:60][N:59]=1)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009570H-Orn(Z)-OHHCID 219736636-(N-Boc-N-2-picolylaminomethyl)nicotinic Acid

生成物 1

HCID 86592262Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithine収率 107.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The compound obtained in Example 8-6 (165.3 mg) was dissolved in DMF (3 ml). After the addition of WSCI hydrochloride (78.5 mg), HOBt (40.1 mg), and the compound obtained in Example 12-3 (90.4 mg), the mixture was stirred for 23 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform and washed with 1 mol/l aqueous solution of hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (10 g, chloroform/methanol=20/1) to obtain the title compound (167.6 mg) as white foam.

後処理

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l aqueous solution of hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue was purified by silica gel column chromatography (10 g, chloroform/methanol=20/1)

出典と根拠

ORDレコード
ord-5d6d23489ab9488382c98bbf6eb9445a
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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