Hydrochloric Acid → O-methyl homoserine methyl ester hydrochloride

HRID 1680594Notes

Reaction equation

HRID 1680594 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C@@H:5]([C:7]([OH:9])=[O:8])[NH2:6].[ClH:10].[CH3:11]O>O1CCOCC1>[ClH:10].[CH3:11][O:8][C:7](=[O:9])[C@H:5]([CH2:4][CH2:3][O:2][CH3:1])[NH2:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 447570(S)-2-amino-4-methoxybutanoic acid

Product 1

HCID 86737808O-methyl homoserine methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 13.3 g of O-methyl homoserine in 370 ml of methanol and 180 ml of a 6 N solution of hydrogen chloride in dioxane is allowed to stand at room temperature for 3 to 4 days. The solvent is removed under reduced pressure and the residue lyophilized to give O-methyl homoserine methyl ester hydrochloride which is represented by the following formula ##STR51## Substitution of an equivalent quantity of O-methyl homoserine methyl ester hydrochloride for the methyl D-methioninate hydrochloride of Example 35 and substantial repetition of the procedures described in Examples 35 through 39 provides methyl DL-2,6-dimethyltyrosyl-DL-O-methylhomoseryl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride which is represented by the following formula ##STR52##

Workup

  1. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-086fd2fd23d74d2ea8e3c8cd67d5a83c
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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