Dichloromethane → HCID 44265775, compound

HRID 2073471Notes

Reaction equation

HRID 2073471 reaction equation
[CH3:1][C@H:2]1[O:18][C:16](=[O:17])[CH2:15][C@@H:14]([O:19][C:20]([CH3:22])=[O:21])[C@H:13]([O:23][CH3:24])[C@@H:12]([O:25][C@@H:26]2[O:31][C@H:30]([CH3:32])[C@@H:29]([O:33][C@@H:34]3[O:39][C@@H:38]([CH3:40])[C@H:37]([O:41][C:42]([CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])[C@@:36]([OH:49])([CH3:48])[CH2:35]3)[C@H:28]([N:50]([CH3:52])[CH3:51])[C@H:27]2[OH:53])[C@@H:11]([CH2:54][CH:55]=[O:56])[CH2:10][C@@H:9]([CH3:57])[C@@H:8]([OH:58])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.C(Cl)Cl>CS(C)=O.C(N(CC)CC)C>[CH3:1][C@H:2]1[O:18][C:16](=[O:17])[CH2:15][C@@H:14]([O:19][C:20]([CH3:22])=[O:21])[C@H:13]([O:23][CH3:24])[C@@H:12]([O:25][CH:26]2[O:31][CH:30]([CH3:32])[CH:29]([O:33][CH:34]3[O:39][CH:38]([CH3:40])[CH:37]([O:41][C:42]([CH2:44][CH:45]([CH3:46])[CH3:47])=[O:43])[C:36]([OH:49])([CH3:48])[CH2:35]3)[CH:28]([N:50]([CH3:52])[CH3:51])[CH:27]2[OH:53])[C@@H:11]([CH2:54][CH:55]=[O:56])[CH2:10][C@@H:9]([CH3:57])[C:8](=[O:58])[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 528216516846-24-52×

Product 1

HCID 44265775HCID 44265775, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8471TriethylamineSolvent

Procedure

10.0 g (12.1 mmol) of leucomycin A3, also known as josamycin, are dissolved in 30 ml of DMSO and 15 ml of triethylamine. To the solution thereby obtained, 5.6 g of sulfur trioxide/pyridine complex (36.3 mmol), dissolved in 40 ml of DMSO, are added at room temperature and under a nitrogen atmosphere. The reaction medium is stirred at room temperature for 3 hours. Approximately 200 g of ice are added and the mixture is filtered: the product thereby obtained is taken up with methylene chloride and the organic phase is washed three times with water; the organic phase is dried over sodium sulfate, filtered and evaporated to dryness. The residue thereby obtained is purified by flash chromatography on a silica column; eluant: CH2Cl2 /MeOH/NH4OH (300:5:0.25). 3.6 g of carbomycin B are obtained.

Workup

  1. customTo the solution thereby obtained
  2. additionare added at room temperature and under a nitrogen atmosphere
  3. filtrationthe mixture is filtered
  4. customthe product thereby obtained
  5. washthe organic phase is washed three times with water
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue thereby obtained
  10. customis purified by flash chromatography on a silica column

Sources & evidence

ORD record
ord-21e631c0b9f94f59b14b0ccec9f36828
Source dataset
uspto-grants-1990_04
Patent number
US04918058

Reaction notes

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