Hydrochloric Acid → L-seryl-L-tyrosylglycyl-L-leucine methyl ester hydrochloride

HRID 65599Notes

Reaction equation

HRID 65599 reaction equation
[CH3:1][O:2][C:3](=[O:42])[C@H:4]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:5][C:6](=[O:37])[CH2:7][NH:8][C:9](=[O:36])[C@H:10]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:11][C:12](=[O:27])[C@H:13]([CH2:25][OH:26])[NH:14]C(OCC1C=CC=CC=1)=O.[ClH:43]>CO.[Pd]>[ClH:43].[CH3:1][O:2][C:3](=[O:42])[C@H:4]([CH2:38][CH:39]([CH3:40])[CH3:41])[NH:5][C:6](=[O:37])[CH2:7][NH:8][C:9](=[O:36])[C@H:10]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:11][C:12](=[O:27])[C@H:13]([CH2:25][OH:26])[NH2:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14802668HCID 14802668, compound

Product 1

HCID 70628285L-seryl-L-tyrosylglycyl-L-leucine methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture consisting of 2.4 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycyl-L-leucine methyl ester, 60 ml. of methanol, 240 mg. of 5% palladium-on-carbon, and 5.4 ml. of 1.26 N hydrogen chloride in methanol is hydrogenated at one atmosphere and 25° C. for one hour. The mixture is then filtered to remove the catalyst, and the filtrate is evaporated to dryness under reduced pressure to give an amorphous solid residue of L-seryl-L-tyrosylglycyl-L-leucine methyl ester hydrochloride; [α]D25 -12.9° (2% in methanol); λmax 278, E11 33.6 (methanol).

Workup

  1. filtrationThe mixture is then filtered
  2. customto remove the catalyst
  3. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8f76f06c3a99446fb29b162ed50a28c0
Source dataset
uspto-grants-1978_12
Patent number
US04128540

Reaction notes

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