HCID 58866148, compound → HCID 58866171, compound

HRID 1354277Notes

Reaction equation

HRID 1354277 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@@H:12]1[N:17]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][C@@H:15]2[O:29]C(C)(C)[O:31][C@H:14]2[C@@H:13]1[OH:34])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.CO>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@@H:13]([OH:34])[C@H:14]([OH:31])[C@@H:15]([OH:29])[CH2:16][N:17]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 58866148HCID 58866148, compound

Product 1

HCID 58866171HCID 58866171, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

The above compound (5-2) (100 mg) was dissolved in a solvent mixture of 1,4-dioxane/methanol (5–15 mL) and a cation exchange resin (Muromac, 2.5 g) was added, and then the mixture was stirred at room temperature for 14 hours. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel medium pressure column chromatography (chloroform:methanol=20:1→10:1) to obtain the titled compound (88 mg).

Workup

  1. additiona cation exchange resin (Muromac, 2.5 g) was added
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel medium pressure column chromatography (chloroform:methanol=20:1→10:1)

Sources & evidence

ORD record
ord-687f7b60653c47829e6cc76a99a1b04a
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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