(Methylthio)acetic acid → Diethyl 2-[(methylsulfenylacetyl)amino]malonate

Reaction equation

[NH2:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:13][S:14][CH2:15][C:16](O)=[O:17]>>[CH3:13][S:14][CH2:15][C:16]([NH:1][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]

Participants

Reactant 2

HCID 75551(Methylthio)acetic acid

HCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl ester

Product 1

HCID 15096452Diethyl 2-[(methylsulfenylacetyl)amino]malonateYield 68.4%

Procedure

Diethyl 2-aminomalonate (3.5 g) and methylsulfenylacetic acid (2.2 g) are treated in the same manner as described in Reference Example 1 to give diethyl 2-[(methylsulfenylacetyl)amino]malonate (3.6 g), m.p. 56°-58° C.

Sources & evidence

ORD record: ord-bac6af6f27894778a169fc047b807f3b
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04882447

Reaction notes

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