Triethylamine → HCID 59922965, compound

HRID 348254Notes

Reaction equation

HRID 348254 reaction equation
[C:1]([N:5]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])(=[O:4])[CH2:2][CH3:3].[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.C(N(CC)CC)C.[O:42]=[C:43]([C@H:49]([CH3:65])[C@@H:50]([O:56][C:57]([O:59][CH2:60][C:61]([Cl:64])([Cl:63])[Cl:62])=[O:58])[C@@H:51]([CH3:55])[CH2:52][CH:53]=[CH2:54])[C:44]([CH3:48])([CH3:47])[CH:45]=[O:46]>C(Cl)Cl>[O:42]=[C:43]([C@H:49]([CH3:65])[C@@H:50]([O:56][C:57]([O:59][CH2:60][C:61]([Cl:62])([Cl:63])[Cl:64])=[O:58])[C@@H:51]([CH3:55])[CH2:52][CH:53]=[CH2:54])[C:44]([CH3:48])([CH3:47])[C@@H:45]([OH:46])[C@H:2]([CH3:3])[C:1]([N:5]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][C:6]1=[O:17])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733696(4S)-4-Benzyl-3-propanoyl-1,3-oxazolidin-2-oneHCID 11211787HCID 11211787, compoundHCID 178418657HCID 178418657, compound

Product 1

HCID 59922965HCID 59922965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of (4S)-3-propionyl-4-benzyloxazolidinone (91 mmol) in 200 mL of CH2Cl2 at 0° C. is treated sequentially with dibutylboron triflate (27 mL) and triethylamine (16.7 mL) at such a rate so as to keep the reaction temperature below 3° C. After stirring for 30 minutes, the mixture is cooled to −78° C. and treated with a solution of (4R,5S, 6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,4,6-tetramethyl-8-nonenal (90 mmol) in 10 mL of CH2Cl2. After 1 hour, the mixture is allowed to warm slowly to 0° C. and stirred an additional 1 hour. The reaction is quenched by addition of 100 mL of pH 7 phosphate buffer and 300 mL of methanol. A mixture of 2:1 methanol/30% aq. H2O2 (300 mL) is then added while maintaining the temperature below 10° C. After stirring for 1 hour, the mixture is concentrated under vacuum to a slurry, which is extracted with ether. The extract is washed sequentially with 5% NaHCO3 and brine, dried over MgSO4, filtered, and evaporated. The product is isolated by silica gel chromatography.

Workup

  1. customthe reaction temperature below 3° C
  2. waitAfter 1 hour
  3. temperatureto warm slowly to 0° C.
  4. stirringstirred an additional 1 hour
  5. customThe reaction is quenched by addition of 100 mL of pH 7 phosphate buffer and 300 mL of methanol
  6. additionA mixture of 2:1 methanol/30% aq. H2O2 (300 mL)
  7. additionis then added
  8. temperaturewhile maintaining the temperature below 10° C
  9. stirringAfter stirring for 1 hour
  10. concentrationthe mixture is concentrated under vacuum to a slurry, which
  11. extractionis extracted with ether
  12. washThe extract is washed sequentially with 5% NaHCO3 and brine
  13. dry with materialdried over MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. customThe product is isolated by silica gel chromatography

Sources & evidence

ORD record
ord-93940fe9693a497fb4a319a29971f430
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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