HCID 178418361, compound → HCID 178479558, compound

HRID 442499Notes

Reaction equation

HRID 442499 reaction equation
[H][H].[Cl:3][C:4]1[C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26][C:5]=1[C:6]([NH:8][C@H:9]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=[O:7]>[Pd].C(O)(=O)C>[ClH:3].[C:6]([NH:8][C@H:9]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)(=[O:7])[C:5]1[NH:26][C:27](=[O:31])[NH:28][C:29](=[O:30])[CH:4]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178513959HCID 178513959, compound

Product 1

HCID 178479558HCID 178479558, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

100 mg of 5% palladium on charcoal in 15 ml of glacial acetic acid are pretreated with hydrogen. Then a solution of 850 mg of 5-chloro-orotyl-L-histidyl-L-prolinamide in 30 ml of glacial acetic acid are added and the mixture is shaken in a hydrogen atmosphere at normal pressure and at room temperature. After consumption of 2 m moles of hydrogen the catalyst is filtered off, the filtrate evaporated to a small volume and treated with absolute ether. The precipitate is separated, washed with ether and dried to give orotyl-L-histidyl-L-prolinamide-hydrochloride in almost quantitative yield.

Workup

  1. customAfter consumption of 2 m moles of hydrogen the catalyst
  2. filtrationis filtered off
  3. customthe filtrate evaporated to a small volume
  4. additiontreated with absolute ether
  5. customThe precipitate is separated
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-04e95433a3f247b58b727d04585e00a8
Source dataset
uspto-grants-1977_08
Patent number
US04045556

Reaction notes

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