HCID 58866187, compound → HCID 58866175, compound

HRID 1354279Notes

Reaction equation

HRID 1354279 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][CH2:28][CH2:29][O:30][CH2:31][CH3:32])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:16][C@@H:15]2[O:33]C(C)(C)[O:35][C@H:14]2[C@@H:13]1[OH:38])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@@H:13]([OH:38])[C@H:14]([OH:35])[C@@H:15]([OH:33])[CH2:16][N:17]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][O:30][CH2:31][CH3:32])=[CH:25][CH:26]=1)(=[O:20])=[O:19])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 58866187HCID 58866187, compound

Product 1

HCID 58866175HCID 58866175, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above compound (5-2) (5.0 g) was dissolved in methanol (130 mL) and a cation exchange resin (Muromac, 23.4 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=20:1→10:1) to obtain the titled compound (4.3 g).

Workup

  1. additiona cation exchange resin (Muromac, 23.4 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-3a9eeda3e7e14c03bfc4bff32137c13e
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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