Potassium Bromide → 6-(2-[2-Aminoacetamido]-2-[p-hydroxyphenyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614152Notes

Reaction equation

HRID 614152 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:3]([NH:5][CH:6]1[C:19](=[O:20])[N:8]2[CH:9]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]12)=[O:4].C(OC(C=C([NH:36][CH2:37][C:38]([O-])=[O:39])C)=O)C.[Na+].[K+].[Br-]>>[NH2:36][CH2:37][C:38]([NH:1][CH:2]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)[C:3]([NH:5][CH:6]1[C:19](=[O:20])[N:8]2[CH:9]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[C:10]([CH3:12])([CH3:13])[S:11][C@H:7]12)=[O:4])=[O:39]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 86736030sodium N-(2-ethoxycarbonyl-1-methylvinyl)-2-aminoacetateHCID 178431937HCID 178431937, compound

Product 1

HCID 1784319406-(2-[2-Aminoacetamido]-2-[p-hydroxyphenyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penamYield 45%

Procedure

The title compound is prepared in 45% yield from 6-(2-amino-2-[p-hydroxyphenyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam and sodium N-(2-ethoxycarbonyl-1-methylvinyl)-2-aminoacetate, using the procedure of Example XC. The product has m.p. 173°-188° C. (dec.) IR (KBr disc): 1785 cm-1 (β-lactam). NMR (DMSO-d6): 7.55-7.10 ppm (m, 2H), 7.00-6.00 ppm (m, 2H), 5.75-5.40 ppm (m, 3H), 5.10 ppm (s, 1H), 3.65 ppm (m, 2H), 1.55 ppm (s, 3H), 0.95 ppm (s, 3H).

Sources & evidence

ORD record
ord-351cf6c8659240bf9f2acbbcd039bbee
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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