Carbon Tetrachloride → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

HRID 863210Notes

Reaction equation

HRID 863210 reaction equation
[CH2:1]([NH:5][C:6](=[O:31])[C@H:7]([CH3:30])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][OH:27])[CH2:2][CH2:3][CH3:4].C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:38].[Na+].C(Cl)Cl>C(#N)C.O.C(OCC)C.O.[Ru](Cl)(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:31])[C@H:7]([CH3:30])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:10]1[CH2:23][C:24]([CH3:29])([CH3:28])[CH2:25][C:26]([OH:38])=[O:27])[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6344DichloromethaneHCID 23667635Sodium periodateHCID 867520963-[3-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyloxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Product 1

HCID 867520953-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

2.9 g of 3-[3-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyloxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide are dissolved in 45 ml of acetonitrile and 45 ml of carbon tetrachloride and the solution is added to a solution of 8.56 g of sodium periodate and 150 mg of ruthenium(III) chloride hydrate in 85 ml of water. After 5 h, the crude product is isolated by extraction with methylene chloride. The crude product is then dissolved in 200 ml of diethyl ether and the solution is stirred with 10 g of Hyflo® and, after 30 min, filtered over Hyflo®. The filtrate is concentrated and the residue is purified by FC (100 g of silica gel, mobile phase S). The title compound is obtained: Rf (S)=0.35; Rt (II)=11.4 min; FABMS: (M+H)+ =457.

Workup

  1. filtrationfiltered over Hyflo®
  2. concentrationThe filtrate is concentrated
  3. customthe residue is purified by FC (100 g of silica gel, mobile phase S)

Sources & evidence

ORD record
ord-88f04996342c4ba4a6e3cb7dda46e3bb
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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