Dimethyl Sulfoxide → (1R,2R,3R,5R,6R)-2-amino-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxamide

HRID 239094

Reaction equation

HRID 239094 reaction equation
CS(C)=O.[NH2:5][C@@:6]1([C:26]#[N:27])[C@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:25])[C:22]([NH2:24])=[O:23].C(=O)([O-])[O-:29].[K+].[K+].OO>O>[NH2:5][C@@:6]1([C:26]([NH2:27])=[O:29])[C@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:25])[C:22]([NH2:24])=[O:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 53236629(1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide

Product 1

HCID 53236628(1R,2R,3R,5R,6R)-2-amino-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxamideYield 324.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a dimethyl sulfoxide (1.2 mL) solution containing 303.0 mg of (1R,2S,3R,5R,6R)-2-amino-2-cyano-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-6-carboxamide (6a), 35.5 mg of potassium carbonate was added under cooling in water bath (13° C. approximately). Subsequently, 0.2 mL of 30 wt % hydrogen peroxide was added thereto and stirred for 30 min. After stirring for 67.5 hrs at room temperature, 3 mL of water was added to the reaction solution and the precipitated solids were filtered and washed with 1.2 mL of water. The resulting solids were dried under reduced pressure at room temperature to obtain 313.2 mg of (1R, 2R,3R,5R,6R)-2-amino-3-[(3,4-dichloro benzyl)oxy]-6-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxamide (7a) as a colorless solid.

Workup

  1. additionwas added
  2. stirringAfter stirring for 67.5 hrs at room temperature
  3. filtrationthe precipitated solids were filtered
  4. washwashed with 1.2 mL of water
  5. customThe resulting solids were dried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-3089721c0edb45699cf35600abdfe9a9
Source dataset
uspto-grants-2014_02
Patent number
US08642777B2

Linked notes

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