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ChemicalBook CAS DataBase List Oxamic acid
471-47-6

Oxamic acid synthesis

9synthesis methods
-

Yield:186268-77-9 2.10 g (75%)

Reaction Conditions:

in tetrahydrofuran;hexane;

Steps:

1.2 Step 2:

Step 2: Synthesis of methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylate A solution of methyl (2S)-1-(1,2-dioxo-2-methoxyethyl)-2-pyrrolidinecarboxylate (2.35 g; 10.90 mmol) in 30 mL of tetrahydrofuran (THF) was cooled to -78° C. and treated with 14.2 mL of a 1.0 M solution of 1,1-dimethylpropylmagnesium chloride in THF. After stirring the resulting homogeneous mixture at -78° C. for three hours, the mixture was poured into saturated ammonium chloride (100·mL) and extracted into ethyl acetate. The organic phase was washed with water, dried, and concentrated, and the crude material obtained upon removal of the solvent was purified on a silica gel column, eluding with 25% ethyl acetate in hexane, to obtain 2.10 g (75%) of the oxamate as a colorless oil. 1H NMR (CDCl3): d 0.88 (t, 3H), 1.22, 1.26 (s, 3H each), 1.75 (dm, 2H), 1.87-2.10 (m, 3H), 25 2.23 (m, 1H), 3.54 (m, 2H), 3.76 (s, 3H), 4.52 (dm, 1H, J=8.4, 3.4).

References:

US2010/317711,2010,A1

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