6-Aminopenicillanic acid → HCID 86734582, compound

HRID 597546Notes

Reaction equation

HRID 597546 reaction equation
[C:1]1([C:7](=[CH:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C@@H:14]1[C:25](=[O:26])[N:16]2[C@@H:17]([C:22]([OH:24])=[O:23])[C:18]([CH3:21])([CH3:20])[S:19][C@H:15]12>>[C:1]1([C:7](=[CH:11][CH3:12])[C:8]([NH:13][CH:14]2[C:25](=[O:26])[N:16]3[CH:17]([C:22]([OH:24])=[O:23])[C:18]([CH3:21])([CH3:20])[S:19][C@H:15]23)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 110826-Aminopenicillanic acidHCID 296649HCID 296649, compound

Product 1

HCID 86734582HCID 86734582, compound

Procedure

In a similar manner to that of Example 17, 2-phenylbut-2-enoic acid (cis isomer) was converted into its acid chloride and coupled with (3S, 5R, 6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid to give the title compound, λmax. (pH 6 phosphate buffer) 234, 345 nm (ε7,200; 4,260), νmax. (nujol) 1770 (β-lactam), τ (d6 -DMSO) values include 0.92 (d, NH), 3.83 (q, 6Hz vinylic proton), 4.3-4.5 (m, 5 and 6 H), 8.42 and 8.52 (gem dimethyl).

Sources & evidence

ORD record
ord-df1397f4681a42b7bc282a0ff57c15e5
Source dataset
uspto-grants-1977_03
Patent number
US04014869

Reaction notes

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