Pyridine → (S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451810Notes

Reaction equation

HRID 451810 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][C@@H:9]([CH2:25][OH:26])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[S:34](Cl)([C:37]1[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=1)(=[O:36])=[O:35]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][C@@H:9]([CH2:25][O:26][S:34]([C:37]1[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 59201667(S)-tert-butyl 4-((R)-5-tert-butoxy-2-(hydroxymethyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201330(S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylateYield 93%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-tert-butyl 4-((R)-5-tert-butoxy-2-(hydroxymethyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (244 mg, 0.63 mmol) in anhydrous DCM (6 mL) was added pyridine (2 mL) and catalytic amount of DMAP, the solution was chilled to 0° C. TsCl (360 mg, 1.88 mmol) was added and stirred at rt overnight. The reaction mixture was diluted with EtOAc (40 mL) and washed with 1 N HCl (two times, 50 ml+20 ml), followed by H2O, aq. NaHCO3, brine, dried over Na2SO4, and filtered. After evaporation, the residue was purified on silica gel column, eluted with 0-20% EtOAc in hexane to afford (S)-tert-butyl 4-((R)-5-tert-butoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (317 mg, yield 93%). MS ESI +ve m/z 564 (M+Na).

Workup

  1. washwashed with 1 N HCl (two times, 50 ml+20 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customAfter evaporation
  5. customthe residue was purified on silica gel column
  6. washeluted with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-1a577402161049568867cbf99cbce2ff
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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