(4s,5r)-n-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid potassium salt → (4S,5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid

HRID 399668Notes

Reaction equation

HRID 399668 reaction equation
[K+].[C:2]([N:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]([O-:22])=[O:21])[O:11][CH:10]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]>C(OCC)(=O)C>[C:2]([N:9]1[C@@H:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:12]([C:20]([OH:22])=[O:21])[O:11][CH:10]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

3

Reactant 1

HCID 69749087(4s,5r)-n-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid potassium salt

Product 1

HCID 22865503(4S,5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(4S,5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid (4a,b) is prepared from the side chain salt as follows. The (4S,5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid potassium salt (1.5 mM) is suspended in ethyl acetate, and the solution washed twice with 5% aqueous sodium bisulfate, once with brine, dried and evaporated. The carboxylic acid is treated with methylene chloride (2 mL), 4-dimethylaminopyridine (48 mg), a solution of the 7-TES-Δ12,13 -iso-baccatin III (3, 0.492 g, 0.702 mM) in toluene (5 mL) plus methylene chloride (8 mL), and 1,3-dicyclohexylcarbodiimide (0.316 g, 1.53 mM). The solution is stirred under an inert atmosphere 2.5 h. The reaction is diluted with ethyl acetate and washed with aqueous sodium bisulfate and aqueous bicarbonate plus brine. The layers are filtered and separated, and the organic layer dried and evaporated. The product is purified by silica gel chromatography in acetone-hexane mixtures. 7-TES-Δ12,13 -iso-baccatin III-13-(4S,5R)-N-Boc-2-(2,4-dimethoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid ester (5a,b) is obtained.

Workup

  1. washthe solution washed twice with 5% aqueous sodium bisulfate, once with brine
  2. customdried
  3. customevaporated
  4. additionThe carboxylic acid is treated with methylene chloride (2 mL), 4-dimethylaminopyridine (48 mg)
  5. additionThe reaction is diluted with ethyl acetate
  6. washwashed with aqueous sodium bisulfate and aqueous bicarbonate plus brine
  7. filtrationThe layers are filtered
  8. customseparated
  9. customthe organic layer dried
  10. customevaporated
  11. customThe product is purified by silica gel chromatography in acetone-hexane mixtures

Sources & evidence

ORD record
ord-29d89f9c5fab4adeb8d4bc5e2db9b307
Source dataset
uspto-grants-1998_10
Patent number
US05821363

Reaction notes

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