p-Toluenesulfonic acid → HCID 86746080, compound

HRID 847305Notes

Reaction equation

HRID 847305 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].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29](S(O)(=O)=O)=[CH:28][CH:27]=1.[C:37](=O)(O)[O-].[Na+]>COC(OC)(C)C>[CH:26]1([CH2:36][C@H:9]2[C@H:10]([CH2:12][C@@H:13]([CH:16]([CH3:17])[CH3:18])[CH:14]=[CH2:15])[O:11][CH2:37][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 86746081HCID 86746081, compound

Product 1

HCID 86746080HCID 86746080, compound

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

1.0 g (2.83 mmol) of (αS,βS)-β-t-butoxycarbonylamino-α-[(S)-2-isopropyl-3-butenyl]cyclohexylpropanol in 15 ml of 2,2-dimethoxypropane and 30 mg of p-toluenesulphonic acid is stirred at room temperature overnight. Thereafter, the reaction mixture is poured into 2N sodium bicarbonate solution and extracted three times with 150 ml of ether each time. The ether extracts are washed with water, combined, dried and evaporated, whereby there are obtained 1.2 g of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S)-2-isopropyl-3-butenyl]-3-oxazolidinecarboxylate as an oil, MS: 393 (M+H)+.

Workup

  1. extractionextracted three times with 150 ml of ether each time
  2. washThe ether extracts are washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-74ac294f9501450ba73c9d578f40d125
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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