Potassium Bromide → HCID 178431927, compound

HRID 614151Notes

Reaction equation

HRID 614151 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([OH:14])=O.[NH2:15][CH:16]1[C:29](=[O:30])[N:18]2[CH:19]([C:24]3[NH:28][N:27]=[N:26][N:25]=3)[C:20]([CH3:23])([CH3:22])[S:21][C@H:17]12.[K+].[Br-]>C(N(CC)CC)C>[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:15][CH:16]1[C:29](=[O:30])[N:18]2[CH:19]([C:24]3[NH:25][N:26]=[N:27][N:28]=3)[C:20]([CH3:22])([CH3:23])[S:21][C@H:17]12)=[O:14]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 139984382-(2-[2-Aminoethoxy]phenyl)acetic acidHCID 178431949HCID 178431949, compound

Product 1

HCID 178431927HCID 178431927, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound is prepared in 64% yield from 2-(2-[2-aminoethoxy]phenyl)acetic acid (U.S. Pat. No. 3,759,905) and 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, by a procedure analogous to that of Example LXXXV. IR (KBr disc): 1780 cm-1 (β-lactam) and 1667 cm-1 (amide I). NMR (in D2O): 7.1 ppm (m, 4H), 5.7 ppm (d, 1H), 5.5 ppm (d, 1H), 5.2 ppm (s, 1H), 3.7-3.3 ppm (m, 4H), 3.1 ppm (q, 12H), 1.6 ppm (s, 3H), 1.2 ppm (t, 18H), 1.0 ppm (s, 3H). The product is a 1:2 complex of the title compound and triethylamine.

Sources & evidence

ORD record
ord-87bfe01513084929b26040142f0cf4a8
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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