HCID 69411572, compound → HCID 58866182, compound

HRID 1354285Notes

Reaction equation

HRID 1354285 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[N:16]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][C@@H:14]2[O:28]C(C)(C)[O:30][C@@H:13]2[C@H:12]1[O:33]C1CCCCO1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([O:8][C:9]([C@H:11]1[C@H:12]([OH:33])[C@H:13]([OH:30])[C@@H:14]([OH:28])[CH2:15][N:16]1[S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)(=[O:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 69411572HCID 69411572, compound

Product 1

HCID 58866182HCID 58866182, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above compound (3) (10.6 g) was dissolved in methanol (110 mL) and a cation exchange resin (Muromac, 50 g) was added, and then the mixture was stirred overnight at room temperature. 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 50:1→30:1→10:1) to obtain the titled compound (7.4 g) as a syrup.

Workup

  1. additiona cation exchange resin (Muromac, 50 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 50:1→30:1→10:1)

Sources & evidence

ORD record
ord-e36b51bf596044c4baab11bc2d3c9705
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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