Hydrogen Peroxide → HCID 19882234, compound

HRID 847308Notes

Reaction equation

HRID 847308 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9](C)[C@@:10](C1CCCCC1)([CH2:12][C@@H:13]([CH:16]([CH3:18])[CH3:17])[CH:14]=[CH2:15])[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:26].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30](S(O)(=O)=O)=[CH:29][CH:28]=1.B.CSC.[OH-].[Na+].OO.CO[C:48](OC)([CH3:50])[CH3:49]>CCCCCC.O.C(O)C>[CH:27]1([CH2:37][CH:9]2[CH:10]([CH2:12][CH:13]([CH:16]([CH3:17])[CH3:18])[CH2:14][CH2:15][OH:26])[O:11][C:48]([CH3:50])([CH3:49])[N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

10

Reactant 6

HCID 784Hydrogen PeroxideHCID 64952,2-DimethoxypropaneHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86746081HCID 86746081, compound

Product 1

HCID 19882234HCID 19882234, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

8.0 g (22.6 mmol) of (αS,βS)-β-t-butoxycarbonylamino-α-[(S)-2-isopropyl-3-butenyl]cyclohexylpropanol are dissolved in 50 ml of 2.2-dimethoxypropane, treated with 0.8 g of p-toluenesulphonic acid hydrate and stirred at room temperature overnight. The crude product (5.34 g; 13.56 mmol) obtained after the usual working-up is dissolved in 200 ml of hexane, treated dropwise rapidly with 0.5 ml of borane-dimethyl sulphide complex (5 mmol based on borohydride) while cooling with ice and thereafter heated to reflux for 1 hour. Then, the reaction mixture is allowed to cool to room temperature, 30 ml of ethanol and 1.67 ml of 3N sodium hydroxide solution are added thereto in succession and finally 1.67 ml of 30% hydrogen peroxide are added dropwise thereto while cooling with ice. After completion of the addition the reaction solution is heated to reflux for 1 hour. Thereafter, the reaction solution is poured into 200 ml of water, extracted with ethyl acetate, the extracts are dried over sodium sulphate and evaporated to dryness under reduced pressure. Flash chromatography of the residue on silica gel with 1:1 mixture of ether and petroleum ether as the eluting agent yields 4 g (71%) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a pale yellow solid, MS: 396 (M-CH3)+.

Workup

  1. customThe crude product (5.34 g; 13.56 mmol) obtained after the
  2. temperaturewhile cooling with ice
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. temperatureto cool to room temperature
  6. temperaturewhile cooling with ice
  7. additionAfter completion of the addition the reaction solution
  8. temperatureis heated
  9. temperatureto reflux for 1 hour
  10. extractionextracted with ethyl acetate
  11. dry with materialthe extracts are dried over sodium sulphate
  12. customevaporated to dryness under reduced pressure
  13. additionFlash chromatography of the residue on silica gel with 1:1 mixture of ether and petroleum ether as the eluting agent

Sources & evidence

ORD record
ord-fd76398ea42248af866d1e33d72243c5
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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