2-azidoacetyl Chloride → p-Nitrobenzyl (5R,6S)-2-(2-azido-acetamido)-6-[(R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate

HRID 847210Notes

Reaction equation

[NH2:1][C:2]1[CH2:3][C@@H:4]2[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:8].[N:26]([CH2:29][C:30](Cl)=[O:31])=[N+:27]=[N-:28]>O1CCCC1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[N:26]([CH2:29][C:30]([NH:1][C:2]1[CH2:3][C@@H:4]2[C@@H:21]([C@H:22]([OH:24])[CH3:23])[C:20](=[O:25])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:8])=[O:31])=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of p-nitrobenzyl (5R,6S)-2-amino-6-[(R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate (35 mg, 0.1 mmol) in anhydrous tetrahydrofuran (2 ml) is cooled to -25° C. and treated with 4-dimethylaminopyridine (15.9 mg, 0.13 mmol) and, dropwise over 5 minutes, with a solution of 2-azidoacetyl chloride (14.3 mg, 0.12 mmol) in tetrahydrofuran (0.5 ml). The resulting mixture is stirred under a nitrogen atmosphere at 0° C. for 4 hours. The mixture is diluted with ethyl acetate, washed with pH 3 phosphate buffer, water, 5% aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and evaporated under vacuum. The residue is chromatographed on a silica gel thin layer preparative plate to afford the title compound.

Workup

washwashed with pH 3 phosphate buffer, water, 5% aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated under vacuum
customThe residue is chromatographed on a silica gel thin layer preparative plate

Sources & evidence

ORD record: ord-060e845235884e65b1c94df0d6113761
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05140030

Reaction notes

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