Dimethyl Sulfoxide → HCID 70148841, compound

HRID 1281210Notes

Reaction equation

HRID 1281210 reaction equation
[O:1]([CH:9]([C:39]([F:47])([F:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:10][CH2:11][C@H:12]1[C@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@@H:14]([OH:24])[CH:13]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.CS(C)=O>ClCCl.C(N(CC)CC)C>[O:1]([CH:9]([C:39]([F:47])([F:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:10][CH2:11][C@H:12]1[C@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C:14](=[O:24])[CH:13]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:37])[CH3:38])=[O:34])[Si:2]([C:5]([CH3:7])([CH3:8])[CH3:6])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 70148109HCID 70148109, compound

Product 1

HCID 70148841HCID 70148841, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of the compound (12-10)(1.09 g) in dichloromethane (2 ml) was subjected to Swan oxydation using oxalyl chloride(2.0M, CH2Cl2 solution, 1.58 ml), a solution of DMSO (0.45 ml) in dichloromethane (10 ml) and triethylamine (0.88 ml). The crude product obtained by the conventional treatment was purified by silica gel chromatography (n-hexane/ethyl acetate=8/2) to give the titled compound (12-11).

Workup

  1. customThe crude product obtained by the conventional treatment
  2. customwas purified by silica gel chromatography (n-hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-145ab79f2a464bc4bf37d13292f4aa02
Source dataset
uspto-grants-2002_09
Patent number
US06452039B1

Reaction notes

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