HCID 18973789, compound → HCID 18973887, compound

HRID 2395035Notes

Reaction equation

HRID 2395035 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH2:30][OH:31])=[O:27])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:33].[Na+]>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:16])=[O:33])=[CH:11][C:10]=1[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([NH:28][CH2:29][CH2:30][OH:31])=[O:27])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18973789HCID 18973789, compoundHCID 23667635Sodium periodate

Product 1

HCID 18973887HCID 18973887, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A slurry of 4-[3-(2-benzyloxy-5-methylthiophenyl)-propyl]-N-(2-hydroxyethyl)benzenecarboxamide (0.22 g) in methanol (10 ml) was added to a stirred solution of sodium metaperiodate (0.113 g) in water (1 ml) maintained at 0° C. by external cooling. The reaction mixture was stirred at 0° C. for 2 hours, then concentrated to a volume of approximately 2 ml. This residue was dissolved in ethyl acetate (10 ml), the ethyl acetate solution was dried (anhydrous magnesium sulphate) and the solution evaporated to dryness. The residue was subjected to chromatography on silica (Merck) eluted with a mixture of methanol/ethyl acetate (1:9 v/v). The only porduct obtained was triturated with ethyl acetate (2 ml) to give 4-[3-(2-benzyloxy-5-methylsulphinylphenyl)propyl]-N-(2-hydroxyethyl)-benzenecarboxamide (mp. 105°-108° C.; 43% yield).

Workup

  1. concentrationconcentrated to a volume of approximately 2 ml
  2. dissolutionThis residue was dissolved in ethyl acetate (10 ml)
  3. dry with materialthe ethyl acetate solution was dried (anhydrous magnesium sulphate)
  4. customthe solution evaporated to dryness
  5. washeluted with a mixture of methanol/ethyl acetate (1:9 v/v)
  6. customThe only porduct obtained
  7. customwas triturated with ethyl acetate (2 ml)

Sources & evidence

ORD record
ord-579b93a2f63b43a884026a39e18ceac8
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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