Acetone → HCID 87527374, compound

HRID 886685Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH2:11]([O:13]/[N:14]=[C:15](/[C:44]1[N:48]=[C:47]([NH2:49])[S:46][N:45]=1)\[C:16]([NH:18][C@@H:19]1[C:26](=[O:27])[N:25]2[C@@H:20]1[S:21][CH2:22][C:23]([S:31][C:32]1[S:33][CH:34]=[C:35]([C:37]3[CH:42]=[CH:41][N+:40]([CH3:43])=[CH:39][CH:38]=3)[N:36]=1)=[C:24]2[C:28]([O-:30])=[O:29])=[O:17])[CH3:12].CC(C)=O>CC(N(C)C)=O>[CH2:11]([O:13]/[N:14]=[C:15](/[C:44]1[N:48]=[C:47]([NH:49][C:1](=[O:3])[CH3:2])[S:46][N:45]=1)\[C:16]([NH:18][C@@H:19]1[C:26](=[O:27])[N:25]2[C@@H:20]1[S:21][CH2:22][C:23]([S:31][C:32]1[S:33][CH:34]=[C:35]([C:37]3[CH:38]=[CH:39][N+:40]([CH3:43])=[CH:41][CH:42]=3)[N:36]=1)=[C:24]2[C:28]([O-:30])=[O:29])=[O:17])[CH3:12]

Participants

Conditions

Temperature: 2.5 °C

Procedure

Acetyl chloride (129.90 g, 1654.77 mmol) and pyridine (23.47 g, 296.67 mmol) were added to a solution of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(amino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene-2-carboxylate (100 g, 164.82 mmol) in dimethylacetamide (1300 ml) and the resulting mixture was stirred at 0-5° C. for 4 to 6 hours. The reaction mixture was then poured into excess acetone to form a slurry which was filtered and dried at room temperature overnight in vacuo to afford 97 g of crude (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene-2-carboxylate. 63% purity by HPLC area % assay (Luna 3 micron C18, 3.0 mm×50 mm; NH4OAc/CH3CN; 1.0 ml/min flow rate)

Workup

customto form a slurry which
filtrationwas filtered
customdried at room temperature overnight in vacuo

Sources & evidence

ORD record: ord-5f3a27efab6e4d61918fc930ec35b910
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247400B2

Reaction notes

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