Dichloromethane → HCID 86699599, compound

HRID 330941Notes

Reaction equation

HRID 330941 reaction equation
O=C1N2[CH2:9][C@@H:4]([CH2:5][CH2:6][C@H:7]2[C:10]([NH:12][O:13][CH2:14][CH2:15][NH:16][S:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:19])=[O:18])=[O:11])N1OS(O)(=O)=O.FC(F)(F)[C:35](O)=[O:36].[CH2:40](Cl)Cl>>[O:36]=[C:35]1[C:6]2[C:7](=[CH:40][CH:9]=[CH:4][CH:5]=2)[C:10](=[O:11])[N:12]1[O:13][CH2:14][CH2:15][NH:16][S:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])(=[O:18])=[O:19]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86699603HCID 86699603, compound

Product 1

HCID 86699599HCID 86699599, compoundYield 23%

Conditions

Temperature
0 °C

Procedure

To a mixture of tert-butyl ({2-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}sulfamoyl)carbamate 81 (0.20 g, 0.40 mmol) in DCM (5.0 mL) was added trifluoroacetic acid (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 0.5 h and at room temperature for 2 h, concentrated and washed with ether. The white solid was collected by centrifugation. The crude product was purified by preparative HPLC to provide Compound 77 (Table 1) (37 mg, 23%) as a white solid.

Workup

  1. concentrationconcentrated
  2. washwashed with ether
  3. customThe white solid was collected by centrifugation
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-479a59681830458594fe6ae6e119f1ea
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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