Proton sponge → tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}pyrrolidine-1-carboxylate

HRID 1865709Notes

Reaction equation

HRID 1865709 reaction equation
[OH:1][C@@H:2]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:3]([CH3:19])[C:4]([N:6]1[C@H:10]([CH3:11])[C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][C:7]1=[O:18])=[O:5].[CH3:32]N(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.C[O+](C)C>ClCCl>[CH3:32][O:1][C@@H:2]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[C@@H:3]([CH3:19])[C:4]([N:6]1[C@H:10]([CH3:11])[C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][C:7]1=[O:18])=[O:5]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 10917041Tert-butyl (2S)-2-{(1R,2R)-1-hydroxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}pyrrolidine-1-carboxylate

Product 1

HCID 10906411tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}pyrrolidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a literature method (Diem, M. J.; Burow, D. F.; Fry, J. L. Journal of Organic Chemistry 42(10), 1977, 1801-1802), to a solution of tert-butyl (2S)-2-{(1R,2R)-1-hydroxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}pyrrolidine-1-carboxylate (0.70 g, 1.6 mmol, from Reference Example 5) in anhydrous dichloromethane (5 mL) is added N,N,N′,N′-tetramethyl-1,8-naphthalenediamine (0.62 g, 2.9 mmol), followed by trimethyloxonium tetrafluoroborate (0.35 g, 2.4 mmol). The resulting reaction mixture is stirred for 24 hours at room temperature, quenched by the addition of ice water (25 mL), and then filtered through a diatomaceous earth pad. The filtrate is evaporated under reduced pressure and then partitioned between diethyl ether and water. The aqueous phase is extracted thrice with diethyl ether. The combined organic extracts are washed with 1M aqueous potassium bisulfate solution, water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 0.69 g (97%) of tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}pyrrolidine-1-carboxylate as a foam.

Workup

  1. customThe resulting reaction mixture
  2. customquenched by the addition of ice water (25 mL)
  3. filtrationfiltered through a diatomaceous earth pad
  4. customThe filtrate is evaporated under reduced pressure
  5. custompartitioned between diethyl ether and water
  6. extractionThe aqueous phase is extracted thrice with diethyl ether
  7. washThe combined organic extracts are washed with 1M aqueous potassium bisulfate solution, water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d3bd0f0ef8541e7b41251a36d659215
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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