p-Toluenesulfonic acid → (4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-one

HRID 2396631Notes

Reaction equation

HRID 2396631 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21][CH2:22][CH:23]([CH3:38])[CH2:24][C@H:25]([CH3:37])[C:26]([N:28]1[C@H:32]([CH:33]([CH3:35])[CH3:34])[CH2:31][O:30][C:29]1=[O:36])=[O:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21][CH2:22][CH:23]([CH3:38])[CH2:24][C@H:25]([CH3:37])[C:26]([N:28]1[C@H:32]([CH:33]([CH3:34])[CH3:35])[CH2:31][O:30][C:29]1=[O:36])=[O:27].[CH:33]([C@@H:32]1[CH2:31][O:30][C:29](=[O:36])[NH:28]1)([CH3:35])[CH3:34]

Participants

6

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 1317192673-[6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(S),4-dimethylhexanoyl)-4-(R)-isopropyl-2-oxazolidinone

Product 2

HCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-oneHCID 1317192673-[6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(S),4-dimethylhexanoyl)-4-(R)-isopropyl-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (E) 3-[6-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(S), 4-dimethylhexanoyl)-4-(R)-isopropyl-2-oxazolidinone (1.3 g) and p-toluenesulphonic acid (0.6 g) in methanol (25 ml) was left at room temperature for 24 hours. The solution was diluted with methylene chloride and washed with dilute aqueous sodium bicarbonate and water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 99.2:0.8 methylene chloride methanol, to give (E) 3-[6-(1,3-dihydro-6-methoxy-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)]-2-(S), 4-dimethylhexanoyl)-4-(R) -isopropyl-2-oxazolidinone, mp 127°-128-C (hexane/methylene chloride).

Workup

  1. washwashed with dilute aqueous sodium bicarbonate and water
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 99.2:0.8 methylene chloride methanol

Sources & evidence

ORD record
ord-679cb93cc41342f281fa9df225072da9
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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