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

HRID 2245218노트

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HRID 2245218 반응식
[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]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 131727991Ac-D-Lys(Z)-D-Pro-D-Val-NH2HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 9864830Ac-D-Lys-D-Pro-D-Val-NH2수율 98.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3310000f698543cbb4a583dcd431bf6b
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683026B2

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