Sodium Chlorite → HCID 69298544, compound

HRID 2196513Notes

Reaction equation

HRID 2196513 reaction equation
[O:1]1C=CC=[C:2]1[C:6]1[N:10]([C:11]2[S:15][C:14]([CH2:16][NH:17][C:18](=[O:29])[C@@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:30]([F:33])([F:32])[F:31])[CH:7]=1.P([O-])(O)(O)=[O:35].[Na+].Cl([O-])=O.[Na+]>C(#N)C.O>[C:24]([O:23][C:22]([NH:21][C@@H:19]([CH3:20])[C:18]([NH:17][CH2:16][C:14]1[S:15][C:11]([N:10]2[C:6]([C:2]([OH:35])=[O:1])=[CH:7][C:8]([C:30]([F:32])([F:31])[F:33])=[N:9]2)=[CH:12][CH:13]=1)=[O:29])=[O:28])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 69095085(S)-tert-butyl 1-((5-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 69298544HCID 69298544, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 24 (70 mg, 0.144 mmol) in acetonitrile (0.42 mL) at 0° C. was added a solution of sodium dihydrogen phosphate (87 mg, 0.722 mmol) in water (0.17 mL). Then a solution of sodium chlorite (131 mg, 1.44 mmol) in water (0.59 mL) was added drop wise. The mixture was allowed to reach 21° C., stirring for 3 h at 21° C. The mixture was quenched with 1N NaOH, washed with CH2Cl2 (2×), and the combined organic phase was extracted with 1N NaOH. The combined aqueous phase was acidified to pH 1 with 1N HCl, extracted with AcOEt, dried (MgSO4) filtered and concentrated to afford 25 (59 mg, 88%) as a yellow solid. LRMS (ESI): calc. 462.1; found 485.2 (MNa)+.

Workup

  1. customto reach 21° C.
  2. customThe mixture was quenched with 1N NaOH
  3. washwashed with CH2Cl2 (2×)
  4. extractionthe combined organic phase was extracted with 1N NaOH
  5. extractionextracted with AcOEt
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-22cd7ec1ccd34a488e42e93b3e1a747b
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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