Phosphate → HCID 66846335, compound

HRID 2369699Notes

Reaction equation

HRID 2369699 reaction equation
[CH:1]1([N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]3[CH2:42][C@@H:41]([C:43]4[CH:54]=[CH:53][C:46]5[O:47][C:48]([CH3:52])([CH3:51])[O:49][CH2:50][C:45]=5[CH:44]=4)[O:40]C3=O)[CH:22]=2)(=[O:14])=[O:13])C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+].P([O-])([O-])([O-])=O>C1COCC1>[CH:1]1([NH:4][S:12]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][CH2:42][C@@H:41]([C:43]4[CH:54]=[CH:53][C:46]5[O:47][C:48]([CH3:51])([CH3:52])[O:49][CH2:50][C:45]=5[CH:44]=4)[OH:40])[CH:22]=3)=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:14])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 23668039Potassium trimethylsilanolateHCID 66844864HCID 66844864, compound

Product 1

HCID 66846335HCID 66846335, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 1,1-dimethylethyl cyclopropyl{[3′-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)-1,1′-biphenyl-2-yl]sulfonyl}carbamate (260 mg) and potassium trimethylsilanolate (420 mg) in THF (10 ml) was heated under reflux for 2 h. The mixture was cooled to 20°, poured into phosphate buffer solution (pH6.5, 50 ml) and extracted with EtOAc (3×30 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4) and the solvent evaporated in vacuo to give a residue which was purified by Biotage. Elution with dichloromethane-ethanol-ammonia (100:8:1) gave the title compound (132 mg). LCMS RT=3.06 min, ES+ve 653 (MH)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was cooled to 20°
  4. extractionextracted with EtOAc (3×30 ml)
  5. washThe combined organic extracts were washed with water (50 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated in vacuo
  8. customto give a residue which
  9. customwas purified by Biotage
  10. washElution with dichloromethane-ethanol-ammonia (100:8:1)

Sources & evidence

ORD record
ord-35a81c6d00d645b9ad86e9345799125b
Source dataset
uspto-grants-2014_04
Patent number
USRE044874E1

Reaction notes

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