2-(Thiophen-3-yl)propanedioic acid → HCID 178431935, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:10]([OH:12])=[O:11])[C:7]([OH:9])=O)=[CH:2]1.[NH2:13][CH:14]1[C:27](=[O:28])[N:16]2[CH:17]([C:22]3[NH:26][N:25]=[N:24][N:23]=3)[C:18]([CH3:21])([CH3:20])[S:19][C@H:15]12.[Na][Na]>>[C:10]([CH:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[C:7]([NH:13][CH:14]1[C:27](=[O:28])[N:16]2[CH:17]([C:22]3[NH:23][N:24]=[N:25][N:26]=3)[C:18]([CH3:20])([CH3:21])[S:19][C@H:15]12)=[O:9])([OH:12])=[O:11]Participants
Procedure
(2.69 mmole) of 2-(3-thienyl)malonic acid (British Pat. No. 1,125,557) with 645 mg. (2.69 mmole) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, according to the procedure of Example CXLVII, affords 810 mg, (67% yield) of 6-(2-carboxy-2-[3-thienyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam as its disodium salt. The infrared spectrum of the product KBr disc) shows absorptions at 1775 cm-1 (β-lactam), 1670 cm-1 (amide I), 1620 cm-1 (carboxylate) and 1525 cm-1 (amide II). The NMR spectrum (D2O) shows absorptions at 7.80-7.00 ppm (multiplet, thienyl hydrogens), 5.88 ppm (doublet, C-6 hydrogen), 5.65 ppm (doublet of doublets, C-5 hydrogen), 5.40 ppm (doublet, C-3 hydrogen), 1.60 ppm (doublet, C-2 methyl hydrogens) and 1.00 ppm doublet, C-2 methyl hydrogens).
Sources & evidence
- ORD record
- ord-578679d2ee8844e3b240df71b2741e70
- Source dataset
- uspto-grants-1979_03
- Patent number
- US04143039
Reaction notes
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