Sodium Bicarbonate → HCID 52950329, compound

HRID 402926Notes

Reaction equation

HRID 402926 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][C@@H:9]([OH:11])[C@H:8]2[C@@H:6]1[C@:7]2([F:16])[C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2].CC1(C)N([O])C(C)(C)CCC1.C(=O)([O-])O.[Na+].Cl[O-].[Na+]>O.ClCCl>[C:1]([O:4][C@H:5]1[CH2:10][C:9](=[O:11])[C@H:8]2[C@@H:6]1[C@:7]2([F:16])[C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 53466235HCID 53466235, compound

Product 1

HCID 52950329HCID 52950329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A dichloromethane (dehydrated, 5 mL) solution of 946 mg (4.07 mmol) of the compound of the formula 3 was cooled to −5° C., 14.0 mg (0.090 mmol) of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO), 102.0 mg (1.21 mmol) of sodium hydrogen carbonate, and 2.0 mL of water were added in sequence, and 3.86 g (5.19 mmol) of a 10% sodium hypochlorite aqueous solution was then added while keeping the internal temperature between −5° C. and 0° C. After stirring at −5° C. to 0° C. for 1 hour, the mixture was separated. The organic layer was washed with 1 mL of water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 899 mg of the compound of the formula 4 was obtained as an oily substance with yellow color.

Workup

  1. additionwas then added
  2. customthe internal temperature between −5° C. and 0° C
  3. customthe mixture was separated
  4. washThe organic layer was washed with 1 mL of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure, 899 mg of the compound of the formula 4
  7. customwas obtained as an oily substance with yellow color

Sources & evidence

ORD record
ord-89be0d9baf074fe7a46e528f3d614472
Source dataset
uspto-grants-2014_06
Patent number
US08742161B2

Reaction notes

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