Methanol → HCID 21104867, compound

HRID 1354283Notes

Reaction equation

HRID 1354283 reaction equation
C(ON[C:10]([C@H:12]1[C@H:17]2[O:18]C(C)(C)[O:20][C@@H:16]2[C@H:15]([OH:23])[CH2:14][N:13]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:11])C1C=CC=CC=1.C[OH:41]>>[OH:18][C@H:17]1[C@H:16]([OH:20])[C@H:15]([OH:23])[CH2:14][N:13]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)(=[O:25])=[O:26])[C@H:12]1[C:10]([OH:41])=[O:11]

Participants

3

Reactant 2

HCID 887MethanolHCID 58866173HCID 58866173, compound

Product 1

HCID 21104867HCID 21104867, compound

Procedure

The above compound (5) (8.68 g) was dissolved in methanol (350 mL) and a cation exchange resin (Muromac, 19.0 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=1:0→30:1→20:1→10:1) to obtain the titled compound (7.35 g) as a colorless powder.

Workup

  1. additiona cation exchange resin (Muromac, 19.0 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=1:0→30:1→20:1→10:1)

Sources & evidence

ORD record
ord-8f3077076563419099404fd1d698fc00
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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