HCID 20381532, compound → HCID 178431932, compound

HRID 1764386Notes

Reaction equation

HRID 1764386 reaction equation
[C:1]1([CH:7]([C:20]([O-:22])=O)[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[CH2:16][CH2:15][CH2:14]3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][CH:24]1[C:37](=[O:38])[N:26]2[CH:27]([C:32]3[NH:36][N:35]=[N:34][N:33]=3)[C:28]([CH3:31])([CH3:30])[S:29][C@H:25]12>>[CH2:15]1[C:14]2[C:13](=[CH:12][C:11]([O:10][C:8]([CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:20]([NH:23][CH:24]3[C:37](=[O:38])[N:26]4[CH:27]([C:32]5[NH:33][N:34]=[N:35][N:36]=5)[C:28]([CH3:30])([CH3:31])[S:29][C@H:25]34)=[O:22])=[O:9])=[CH:19][CH:18]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 20381532HCID 20381532, compoundHCID 178431949HCID 178431949, compound

Product 1

HCID 178431932HCID 178431932, compoundYield 63%

Procedure

(2.0 mmole) of 5-indanyl 2-phenylmalonate with 480 mg. (2.0 mmole) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, according to the procedure of Example CXLVII affords 680 mg. (63% yield) of 6-(2-[5-indanyloxycarbonyl]-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam as its sodium salt. The infrared spectrum (KBr disc) of the product shows absorption bands at 1780 cm-1 (β-lactam), 1705 cm-1 (ester), 1680 cm-1 (amide I) and 1565 cm-1 (amide II). The NMR spectrum (D2O) shows absorption bands at 7.80-6.80 ppm (multiplet, aromatic hydrogens), 5.70 ppm (multiplet, C-5 and C-6 hydrogens), 5.25 ppm (doublet, C-3 hydrogen), 2.60-2.00 ppm (multiplet, C-1 and C-3 indanyl hydrogens), 2.00-1.80 ppm (multiplet, C-2 indanyl hydrogens), 1.35 ppm (doublet, C-2 methyl hydrogens) and 0.90 ppm (doublet C-2 methyl hydrogens).

Workup

  1. customaffords 680 mg

Sources & evidence

ORD record
ord-a0219f472cbb456194419ebf3e42f006
Source dataset
uspto-grants-1978_09
Patent number
US04115385

Reaction notes

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