Hydrochloric Acid → L-tryptophyl-L-seryl-L-tyrosine methyl ester hydrochloride

HRID 1763725Notes

Reaction equation

HRID 1763725 reaction equation
[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[NH:5][C:6](=[O:35])[C@H:7]([CH2:33][OH:34])[NH:8][C:9](=[O:32])[C@H:10]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:11]C(OCC1C=CC=CC=1)=O.CO.[ClH:47]>[Pd].O1CCCC1>[ClH:47].[CH3:1][O:2][C:3](=[O:44])[C@H:4]([CH2:36][C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=1)[NH:5][C:6](=[O:35])[C@H:7]([CH2:33][OH:34])[NH:8][C:9](=[O:32])[C@H:10]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH2:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54186548HCID 54186548, compound

Product 1

HCID 70617527L-tryptophyl-L-seryl-L-tyrosine methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3.1 g. of Nα -benzyloxycarbonyl-L-trytophyl-L-seryl-L-tyrosine methyl ester and 200 mg. of 20% palladium on carbon is added 75 ml. of methanol containing 1.7 ml. of 3N hydrogen chloride in tetrahydrofuran and the reaction is stirred under an atmosphere of hydrogen for two and a half hours. The mixture is filtered to remove the catalyst and the filtrate is evaporated under reduced pressure to give a residue of L-tryptophyl-L-seryl-L-tyrosine methyl ester hydrochloride which is suitable for use without further purification.

Workup

  1. additionTo a mixture of 3.1 g
  2. filtrationThe mixture is filtered
  3. customto remove the catalyst
  4. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-ff3903e65c1846ec828462fa69a4cdc2
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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