Acetic Acid → Ac-D-Lys-D-Pro-D-Val-NH2

HRID 2245218ノート

反応式

HRID 2245218 の反応式
[NH:1]([C:35]([CH3:37])=[O:36])[C@@H:2]([C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@@H:21]1[C:22]([NH:24][C@@H:25]([C:29]([NH2:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.CC(O)=O.O.[H][H]>CCO.[Pd]>[NH:1]([C:35]([CH3:37])=[O:36])[C@@H:2]([C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@@H:21]1[C:22]([NH:24][C@@H:25]([C:29]([NH2:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:23])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 131727991Ac-D-Lys(Z)-D-Pro-D-Val-NH2HCID 178418361HCID 178418361、化合物

生成物 1

HCID 9864830Ac-D-Lys-D-Pro-D-Val-NH2収率 98.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

107 g of Ac-D-Lys(Z)-D-Pro-D-Val-NH2 are dissolved in 535 ml of EtOH, added with 214 ml of AcOH and of 21.4 g of Pd/C at 10% at 50% water. The hydrogenation is conducted at 20° C., under a 1 bar hydrogen pressure for 16 hours. The reaction completion is CCM controlled. The catalyst is filtered and the filtrate is vacuum concentrated until refusal. The residue is recovered with 107 ml of EtOH, added with 430 ml of iPrOH and the blend is heated at 50° C., then added dropwise at 50° C. with 1500 ml of diisopropyl ether. The expected product crystallizes. The medium is cooled down to 20° C. and stirred for 1 hour. The solid is filtered and washed with 500 ml of diisopropyl ether before being vacuum dried at 25° C. so to provide 78.3 g of Ac-D-Lys-D-Pro-D-Val-NH2 under the form of an acetate salt (yield 85.4%). The thus obtained product purity is HPLC controlled.

後処理

  1. filtrationThe catalyst is filtered
  2. concentrationconcentrated until refusal
  3. customThe residue is recovered with 107 ml of EtOH
  4. additionadded with 430 ml of iPrOH
  5. additionadded dropwise at 50° C. with 1500 ml of diisopropyl ether
  6. customThe expected product crystallizes
  7. temperatureThe medium is cooled down to 20° C.
  8. filtrationThe solid is filtered
  9. washwashed with 500 ml of diisopropyl ether
  10. customdried at 25° C. so

出典と根拠

ORDレコード
ord-3310000f698543cbb4a583dcd431bf6b
出典データセット
uspto-grants-2010_03
特許番号
US07683026B2

反応ノート

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