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

HRID 2245218Notes

Reaction equation

HRID 2245218 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 9864830Ac-D-Lys-D-Pro-D-Val-NH2Yield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3310000f698543cbb4a583dcd431bf6b
Source dataset
uspto-grants-2010_03
Patent number
US07683026B2

Reaction notes

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