Chlorosuccinimide → HCID 86701375, compound

HRID 1424516Notes

Reaction equation

HRID 1424516 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][CH:18]1[CH2:19][CH2:20][CH:21]2[CH:26]=[N:27][OH:28])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.N1C=CC=CC=1>[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:18]1[CH2:19][CH2:20][C@H:21]2[C:26]([Cl:8])=[N:27][OH:28])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86706185HCID 86706185, compound

Product 1

HCID 86701375HCID 86701375, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

NCS (295 mg, 2.2 mmol) was added to a solution of 6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbaldehyde oxime (560 mg, 2.0 mmol) in dry DCM (15 mL) at rt. Pyridine (one drop) was then added, and the reaction mixture was stirred at rt for 18 hrs. The solution was evaporated to afford (2S,5R)-6-(benzyloxy)-N-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbimidoyl chloride, which was directly used in the next step. ESI-MS (EI+, m/z): 274 [M-Cl]+.

Workup

  1. customThe solution was evaporated

Sources & evidence

ORD record
ord-7e444b7c9f5a48f2a7b98192d2ccd3fc
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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