N-Benzylphenethylamine → Penicillanic Acid

HRID 1065737Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:31])[S:22](=O)(=O)[C@@H:21]2[CH2:25][C:26](=[O:27])[N:20]2[C@H:19]1[C:28]([OH:30])=[O:29]>>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:31])[S:22][C@@H:21]2[CH2:25][C:26](=[O:27])[N:20]2[C@H:19]1[C:28]([OH:30])=[O:29]

Participants

Reactant 2

HCID 65055N-Benzylphenethylamine

HCID 130313Sulbactam

Product 2

HCID 6891Penicillanic Acid

HCID 65055N-Benzylphenethylamine

Procedure

The 1:2 N,N'-dibenzylethylenediamine salt of penicillanic acid 1,1-dioxide is the salt formed from N,N'-dibenzylethylenediamine and two molar equivalents of penicillanic acid 1,1-dioxide; the N-benzyl-2-phenylethylamine salt of penicillanic acid 1,1-dioxide is the salt formed from N-benzyl-2-phenylethylamine and one molar equivalent of penicillanic acid, 1,1-dioxide; and the dibenzylamine salt of penicillanic acid 1,1-dioxide is the salt formed from dibenzylamine and one molar equivalent of penicillanic acid 1,1-dioxide. N,N'-dibenzylethylenediamine is also known as benzathine and as DBED; N-benzyl-2-phenylethylamine is also known as benethamine.

Sources & evidence

ORD record: ord-40ececf7437748739ad053fb043731cc
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04331599

Reaction notes

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