Methanol → HCID 18323818, compound

HRID 1251483Notes

Reaction equation

HRID 1251483 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:21][CH3:22])[C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[N:14]=1.C[OH:24]>O>[CH3:1][S:2]([C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:21][CH3:22])[C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[N:14]=1)=[O:24]

Participants

4

Reactant 2

HCID 887MethanolHCID 10686839HCID 10686839, compound

Product 1

HCID 18323818HCID 18323818, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The sulfide of Example 35, (300 mg, 0.95 mmoles), was reacted with 300 mg (1.41 mmoles) NaIO4 in 6 mL MeOH and 3 mL water at 25° C. for 24 h. The reaction mixture was partitioned between 100 mL EtOAc and 25 mL water and the EtOAc extract was washed with water, brine, dried and stripped in vacuo. The residue was purified by silica gel chromatography using 1:1 EtOAc/hexanes as eluent to give 220 mg product, (70% yield); mp 144-146° C. Elemental analysis for C18H25N3O5: Theory C, 65.22; H, 7.60; N, 12.68; S, 9.67. Found: C, 65.12; H, 7.63; N, 12.48; S, 9.71.

Workup

  1. customThe reaction mixture was partitioned between 100 mL EtOAc and 25 mL water
  2. extractionthe EtOAc extract
  3. washwas washed with water, brine
  4. customdried
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-62cbf729806f44aaa5672e8d0e94223e
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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