7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → HCID 86736112, compound

HRID 1112456Notes

Reaction equation

[CH:1]([C:3]1[N:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1)=[O:2].C(N(CC)CC)C.Cl[C:20](OCC(C)C)=[O:21].[NH2:27][CH:28]1[C:35](=[O:36])[N:34]2[CH:29]1[S:30][CH2:31][C:32]([CH3:40])=[C:33]2[C:37]([OH:39])=[O:38]>O1CCCC1>[CH:1]([C:3]1[N:4]([CH2:8][C:9]([NH:27][C:28]2([O:21][CH3:20])[C:35](=[O:36])[N:34]3[CH:29]2[S:30][CH2:31][C:32]([CH3:40])=[C:33]3[C:37]([OH:39])=[O:38])=[O:11])[CH:5]=[CH:6][CH:7]=1)=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (2-formyl-1-pyrryl)acetic acid (0.02 m) and triethylamine (0.02 m) in tetrahydrofuran (THF) is cooled to 0° C. While stirring, isobutyl chloroformate (0.02 m) is added and the temperature is maintained at 0° C for 15 minutes. A cold solution of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (0.02 m) and triethylamine (0.02 m) in 50% aqueous THF is added to the previous solution with stirring.

Workup

stirringwith stirring

Sources & evidence

ORD record: ord-b88a614bd8764c49bdca59c4243baa44
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04122260

Reaction notes

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