Hydrogen Peroxide → HCID 68639742, compound

HRID 1354982Notes

Reaction equation

HRID 1354982 reaction equation
C(S[C:9](=[O:49])[CH:10]([CH:18]1[CH:25]=[CH:24][CH2:23][CH:22]([CH:26]([NH:39]C(OC(C)(C)C)=O)[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34]C(C)(C)C)=[CH:30][CH:29]=2)[O:21][Si](C)(C)[O:19]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C1C=CC=CC=1.N1C=CC=CC=1.[Li+].[OH-:57].OO>C1COCC1>[NH2:39][CH:26]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)[CH:22]([OH:21])[CH2:23]/[CH:24]=[CH:25]\[CH:18]([OH:19])[CH:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([OH:57])=[O:49]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1049PyridineHCID 3939Lithium HydroxideHCID 72447997HCID 72447997, compound

Product 1

HCID 68639742HCID 68639742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compounds 8 were silyl deprotected in parallel with HF/pyridine in THF at 0° C. for 30 minutes according to the reported procedure. The products were purified by flash chromatography (4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) to give the desilylated products in the following yields: (S,S,S,R) 83%, (S,S,R,R) 67%, (S,R,R,R) 85%, (S,R,S,R) 81%. To hydrolyze the thioester to the free acid, these products were dissolved in THF (40 ml/mmole) in parallel, and a 1:1 mixture of 0.2 N LiOH (aq, 4 eq.) and 30% H2O2 (aq) was added to each. The reactions were stirred at room temperature for 3 hours, then cooled to 0° C. and quenched with 2N NaHSO3 (aq, 5 mL per ml 30% H2O2). The reactions were extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under vacuum to give clean 15 in the following yields: (S,S,S,R)-15 100%, (S,S,R,R)-15 96%, (S,R,R,R)-15 100%, (S,R,S,R)-15 100%.

Workup

  1. customat 0° C.
  2. customfor 30 minutes
  3. customThe products were purified by flash chromatography (4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc)
  4. customto give the desilylated products in the
  5. customfollowing yields
  6. additionwas added to each
  7. temperaturecooled to 0° C.
  8. customquenched with 2N NaHSO3 (aq, 5 mL per ml 30% H2O2)
  9. extractionThe reactions were extracted with EtOAc
  10. washwashed with brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under vacuum
  14. customto give clean 15 in the
  15. customfollowing yields

Sources & evidence

ORD record
ord-7d556b7d16f44b2eb1508ff8a82df282
Source dataset
uspto-grants-2007_05
Patent number
US07223888B2

Reaction notes

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