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

HRID 2083822Notes

Reaction equation

HRID 2083822 reaction equation
CO.[ClH:3].[CH3:4][O:5][C:6](=[O:47])[C@H:7]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=1)[NH:8][C:9](=[O:38])[C@H:10]([CH2:36][OH:37])[NH:11][C:12](=[O:35])[C@H:13]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[NH:14]C(OCC1C=CC=CC=1)=O>O1CCCC1.[Pd]>[ClH:3].[CH3:4][O:5][C:6](=[O:47])[C@H:7]([CH2:39][C:40]1[CH:41]=[CH:42][C:43]([OH:46])=[CH:44][CH:45]=1)[NH:8][C:9](=[O:38])[C@H:10]([CH2:36][OH:37])[NH:11][C:12](=[O:35])[C@H:13]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)[NH2:14]

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

Methanol (75 ml.) containing 1.7 ml. of 3N hydrogen chloride in tetrahydrofuran is added to a mixture of 3.1 g. of Nα -benzyloxycarbonyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester and 200 mg. of 20% palladium-on-carbon 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. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-6c77b608e8c14205a382810b8a848044
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

Loading…