Acetic Acid → L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine sulfoxide hydrochloride

HRID 614206Notes

Reaction equation

HRID 614206 reaction equation
C(OC([NH:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:37]([NH:39][C@H:40]([C:46]([OH:48])=[O:47])[CH2:41][CH2:42][S:43]([CH3:45])=[O:44])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])=[O:23])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=O)(C)(C)C.C(O)(=O)C.[ClH:53].CCOCC>O1CCOCC1>[ClH:53].[NH2:8][C@H:9]([C:18]([NH:20][CH2:21][C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:37]([NH:39][C@H:40]([C:46]([OH:48])=[O:47])[CH2:41][CH2:42][S:43]([CH3:45])=[O:44])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])=[O:23])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22807105N-t-butoxycarbonyl-L-tyrosyl-glycylglycyl-L-phenylalanyl-L-methionine sulfoxide

Product 1

HCID 22807102L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine sulfoxide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12.0 Parts N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine sulfoxide is suspended in 100 parts by volume acetic acid and treated with 50 parts by volume 6 M HCl in dioxane. The resulting mixture is stirred at room temperature for two hours and then stripped of solvent under reduced pressure. Trituration of the residue with ether affords solid L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine sulfoxide hydrochloride. This compound is represented by the following formula. ##STR6##

Sources & evidence

ORD record
ord-838cb42d6e294829811c02d046070c7f
Source dataset
uspto-grants-1979_03
Patent number
US04144228

Reaction notes

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