Hydrochloric Acid → HCID 20770842, compound

HRID 1296049Notes

Reaction equation

HRID 1296049 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][C:17](=O)[N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH3:27].O=P(Cl)(Cl)Cl.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:8][C:7]=1[CH3:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20770840HCID 20770840, compound

Product 1

HCID 20770842HCID 20770842, compound

Procedure

Compound 63A was dissolved POCl3 (250 mg, 1.6 mmol) and stirred for 15 minutes. The reaction was concentrated by blowing with nitrogen followed by concentration under vacuum. The intermediate was dissolved in 5 ml dimethoxyethane and cooled to ca. 5 C. Sodium borohydride (20 mg, 0.53 mmol) was added followed by warming to room temp. After 3 h 25 ml 2N HCl was added and heated to boiling for 1 minute. Saturated sodium bicarbonate was added to pH ca. 7–8. The crude product was extracted with 2×20 ml ethyl acetate, dried over anhydrous sodium sulfate, decanted and concentrated. Liquid chromatography gave the title product as a clear colorless oil. MS m/z 391 (M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. concentrationfollowed by concentration under vacuum
  3. dissolutionThe intermediate was dissolved in 5 ml dimethoxyethane
  4. temperaturecooled to ca. 5 C
  5. temperatureheated
  6. waitto boiling for 1 minute
  7. extractionThe crude product was extracted with 2×20 ml ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customdecanted
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3f9b053ff4b94436a16acb7461c07a1c
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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