Z-Val-Pro-Val-Pro Ara-C → H-Val-Pro-Val-Pro Ara-C

HRID 882692Notes

Reaction equation

HRID 882692 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:6]([N:8]1[CH2:29][CH2:28][CH2:27][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH:40]1[C:46]([NH2:47])=[N:45][C:43](=[O:44])[N:42]([C@@H:48]2[O:52][C@H:51]([CH2:53][OH:54])[C@@H:50]([OH:55])[C@@H:49]2[OH:56])[CH:41]=1>CO.[Pd]>[NH2:1][C@H:2]([C:6]([N:8]1[CH2:29][CH2:28][CH2:27][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([OH:23])=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH:40]1[C:46]([NH2:47])=[N:45][C:43](=[O:44])[N:42]([C@@H:48]2[O:52][C@H:51]([CH2:53][OH:54])[C@@H:50]([OH:55])[C@@H:49]2[OH:56])[CH:41]=1

Participants

4

Reactant 1

HCID 131729867Z-Val-Pro-Val-Pro Ara-C

Product 1

HCID 131729868H-Val-Pro-Val-Pro Ara-CYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the corresponding Ara-C-tetrapeptide-Z-protected (D) (24.7 mg, 0.03 mmol) in methanol containing Pd/C (10% wt/wt) (11.5 mg) was hydrogenated at 25 psi at room temperature for 2 h. The reaction mixture was filtered, and the filtrate was evaporated to dryness, under reduced pressure, to give D (90% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness, under reduced pressure
  3. customto give D (90% yield)

Sources & evidence

ORD record
ord-da042871c6a0448daa49d5d6ff450a0a
Source dataset
uspto-grants-2012_08
Patent number
US08236756B2

Reaction notes

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