2-Methoxypropene → HCID 57140265, compound

HRID 964331Notes

Reaction equation

HRID 964331 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:10]([OH:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[S:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]1(C)[CH:30]=CC(S([O-])(=O)=O)=C[CH:26]=1.[NH+]1C=CC=CC=1.COC(C)=C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[S:12])[O:18][C:25]1([CH3:30])[CH3:26])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 83002-MethoxypropeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57190379HCID 57190379, compound

Product 1

HCID 57140265HCID 57140265, compoundYield 1,268.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of t-butyl (2R,3S)-3-tertbutoxycarbonylamino-2-hydroxy-3-phenylthiopropionate (0.060 g, 0.17 mmol) in toluene (8.0 ml) was treated with pyridinium p-toluene sulfonate (2.14 mg) and freshly distilled 2-methoxypropene (0.384 ml). The mixture was stirred at RT for 5 min, and at 80° C. for 4 h. After dilution with ethyl acetate (8 ml), the organic phase was washed with aqueous NaHCO3 sat. solution (3 ml), brine (2×3 ml), dried (Na2SO4), and evaporated to give a crude mixture. Purification via flash chromatography (hexanes-ethyl ether 95:5) gave pure t-butyl [(4S,5R)-N-tertbutoxycarbonyl-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]thiocarboxylate (42.5 mg, 65.6%).

Workup

  1. waitat 80° C. for 4 h
  2. washAfter dilution with ethyl acetate (8 ml), the organic phase was washed with aqueous NaHCO3 sat. solution (3 ml), brine (2×3 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a crude mixture
  6. customPurification via flash chromatography (hexanes-ethyl ether 95:5)

Sources & evidence

ORD record
ord-921a9fa745194599b9e624afd44bda37
Source dataset
uspto-grants-1998_06
Patent number
US05767282

Reaction notes

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