Phosphate → HCID 66617175, compound

HRID 1713000Notes

Reaction equation

HRID 1713000 reaction equation
[C:1]([N:18]1[CH2:23][CH:22]([CH2:24][OH:25])[NH:21][C:20](=[O:26])[C:19]1([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].P([O-])([O-])([O-])=[O:36].CC1(C)N([O])C(C)(C)CCC1.Cl([O-])=O.[Na+].Cl[O-].[Na+].S([O-])(O)=O.[Na+]>C(#N)C.C(OCC)(=O)C>[C:1]([N:18]1[C:19]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[C:20](=[O:26])[NH:21][CH:22]([C:24]([OH:36])=[O:25])[CH2:23]1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

9

Reactant 6

HCID 1061PhosphateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 23665763Sodium BisulfiteHCID 23668197Sodium ChloriteHCID 66617235HCID 66617235, compound

Product 1

HCID 66617175HCID 66617175, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
43 °C

Procedure

To a solution of 8 mmol alcohol (89) in 81 mL of acetonitrile kept at room temperature, is added phosphate buffer solution (prepared with 0.72 g of sodium phosphate monobasic and 1.43 g of sodium phosphate dibasic in 29.5 mL of water), followed by the addition of 0.33 g (2.1 mmol) of TEMPO, and 1.86 g (16.5 mmol) of sodium chlorite, and the biphasic solution is placed in an oil bath kept at 43° C. A solution of 4.3 mL (2.6 mmol) of sodium hypochlorite solution (prepared by mixing 1.9 mL of 10-13% sodium hypochlorite solution, and 2.4 mL of water) is added slowly. The reaction is stirred at 43° C. for 4 hours, cooled to room temperature, 20 mL of 10% sodium hydrogen sulfite added, stirred for 10 minutes, diluted with 50 mL of ethyl acetate, and the layers separated. The organic layer is washed with 1×10 mL of brine, 1×10 mL of 1N hydrochloric acid solution, dried over sodium sulfate, and concentrated. Compound (90) is purified by silica gel column chromatography.

Workup

  1. customkept at room temperature
  2. customthe biphasic solution is placed in an oil bath
  3. customkept at 43° C
  4. temperaturecooled to room temperature
  5. stirringstirred for 10 minutes
  6. customthe layers separated
  7. washThe organic layer is washed with 1×10 mL of brine, 1×10 mL of 1N hydrochloric acid solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customCompound (90) is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6e4dd83ce7c34f63b7cb104895e61e83
Source dataset
uspto-grants-2010_09
Patent number
US07795221B2

Reaction notes

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