Sodium Acetate → HCID 178513957, compound

HRID 442498Notes

Reaction equation

HRID 442498 reaction equation
C([O-])(=[O:3])C.[Na+].[H][H].Cl[C:9]1[C:34](=[O:35])[NH:33][C:32](=[O:36])[NH:31][C:10]=1[C:11]([NH:13][C@H:14]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:12]>[Pd].O>[OH2:3].[C:11]([NH:13][C@H:14]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)(=[O:12])[C:10]1[NH:31][C:32](=[O:36])[NH:33][C:34](=[O:35])[CH:9]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 178418361HCID 178418361, compound3×HCID 178513959HCID 178513959, compound

Product 1

HCID 178513957HCID 178513957, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

To 15 ml of water are added 165 mg of anhydrous sodium acetate and 100 mg of 5% palladium on charcoal. On a shaking apparatus the mixture is treated with hydrogen until the absorption stops. Then a solution of 850 mg of 5-chloro orotyl-L-histidyl-L-prolinamide in 30 ml of water is added and shaking in a hydrogen atmosphere is continued at normal pressure and room temperature until 2m moles (about 50 ml) of hydrogen are consumed. The catalyst is filtered off, the filtrate is extracted two times with ether and then the aqueous layer is evaporated at room temperature under reduced pressure to a volume of about 2 to 3 ml and diluted with two times it volume of methanol. This solution is poured on a column of 150 g of basic aluminium oxide, followed by elution with methanol/water (2:1), controlled by measuring the ultraviolet absorption spectrum at 254 nm. The fractions containing the main product are combined, evaporated under reduced pressure and finally lyophylized. Thus 780 mg (96 % of the theoretical yield) of orotyl-L-histidyl-L-prolinamide hydrate (i.e., the same product as prepared in Example 2) are obtained.

Workup

  1. customare consumed
  2. filtrationThe catalyst is filtered off
  3. extractionthe filtrate is extracted two times with ether
  4. customthe aqueous layer is evaporated at room temperature under reduced pressure to a volume of about 2 to 3 ml
  5. additiondiluted with two times it volume of methanol
  6. additionThis solution is poured on a column of 150 g of basic aluminium oxide
  7. washfollowed by elution with methanol/water (2:1)
  8. customthe ultraviolet absorption spectrum at 254 nm
  9. additionThe fractions containing the main product
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-563fff45ba284942aa229dec1666834e
Source dataset
uspto-grants-1977_08
Patent number
US04045556

Reaction notes

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