Hydrochloric Acid → HCID 70604781, compound

HRID 1764392Notes

Reaction equation

Cl.C1(CC([NH:11][CH:12]2[C:33](=[O:34])[N:14]3[CH:15]([C:20]4[N:24]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:23]=[N:22][N:21]=4)[C:16]([CH3:19])([CH3:18])[S:17][C@H:13]23)=O)C=CC=CC=1.[K+].[Br-]>>[NH2:11][CH:12]1[C:33](=[O:34])[N:14]2[CH:15]([C:20]3[N:24]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:30])([CH3:29])[CH3:31])[N:23]=[N:22][N:21]=3)[C:16]([CH3:18])([CH3:19])[S:17][C@H:13]12

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 253877Potassium Bromide

HCID 70605336HCID 70605336, compound

Product 1

HCID 70604781HCID 70604781, compoundYield 90%

Procedure

The title compound is prepared as its hydrochloride, in 90% yield, from 6-(2-phenylacetamido)-2,2-dimethyl-3-(1-[pivaloyloxymethyl]tetrazol-5-yl)penam, using the method of Example CLXXVI. The infrared spectrum (KBr disc) shows absorptions at 1780 cm-1 (β-lactam) and 1740 cm-1 (ester). The NMR spectrum (DMSO-d6) shows absorptions at 6.71 ppm (singlet, 2H, pivaloyloxy methylene hydrogens), 5.88 ppm (singlet, 1H, C-3 hydrogen), 5.83 ppm (doublet, 1H, C-5 hydrogen), 5.20 ppm (doublet, 1H, C-6 hydrogen), 1.80 ppm (singlet, 3H, C-2 methyl hydrogens), 1.20 ppm (singlet, 9H, t-butyl hydrogens) and 1.16 ppm (singlet, 3H, C-2 methyl hydrogens).

Sources & evidence

ORD record: ord-30af4a82bcdc4989b40678d9a08de2c5
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04115385

Reaction notes

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