7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → (Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 839105

Reaktionsgleichung

Reaktionsgleichung von HRID 839105
[CH3:1][C:2]1[CH2:9][S:8][CH:7]2[N:4]([C:5](=[O:11])[CH:6]2[NH2:10])[C:3]=1[C:12]([OH:14])=[O:13].ClC[CH2:17][C:18]([CH3:23])([CH3:22])[C:19]([O-:21])=[O:20].[C:24](OCC1CSC2N(C(=O)C2N)C=1C(O)=O)(=O)C.ClCOC(=O)CC>>[C:19]([O:21][CH2:24][O:13][C:12]([C:3]1[N:4]2[CH:7]([S:8][CH2:9][C:2]=1[CH3:1])[CH:6]([NH2:10])[C:5]2=[O:11])=[O:14])(=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17]

Komponenten

5

Edukt 4

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 221144Chloromethyl propionateHCID 217530474-Chloro-2,2-dimethylbutanoate

Produkt 1

HCID 119617(Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Versuchsvorschrift

When in the procedure of Example 8 appropriate amounts of 3-methyl-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and chloromethylpivalate are substituted respectively for 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and chloromethylpropionate, 3-methyl-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-935a99ac1d5a44c8828f0b6ab92dbcf4
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093802

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