Dimethyl Sulfoxide → HCID 88174234, compound

HRID 1281213Notes

Reaction equation

HRID 1281213 reaction equation
[C:1]([O:4][C@H:5]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C@H:8]([CH2:24][OH:25])[C@H:7]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH2:6]1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CS(C)=O>ClCCl.C(N(CC)CC)C>[C:1]([O:4][C@H:5]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])[C@@H:8]([CH:24]=[O:25])[C@H:7]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 70147894HCID 70147894, compound

Product 1

HCID 88174234HCID 88174234, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution (10 ml) of the compound (13-4)(3.18 g) in dichloromethane was subjected to Swan oxydation using oxalyl chloride(2M, CH2Cl2 solution, 8.78 ml), a solution (20 ml) of DMSO (2.49 ml) in dichloromethane and triethylamine (5.87 ml). The crude product obtained by the conventional treatment was purified by silica gel chromatography (n-hexane/ethyl acetate=7/3) to give the titled compound (13-5).

Workup

  1. customThe crude product obtained by the conventional treatment
  2. customwas purified by silica gel chromatography (n-hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-09f89d6550c941cfb5a786532b8fe12a
Source dataset
uspto-grants-2002_09
Patent number
US06452039B1

Reaction notes

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