Tetrahydrofuran → HCID 11270377, compound

HRID 902966Notes

Reaction equation

HRID 902966 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12][C:11]=2[CH:27]=1)[CH3:2].C1C[O:33]CC1>>[CH2:28]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12](=[O:33])[C:11]=2[CH:27]=1)[CH3:29]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 11429912HCID 11429912, compound

Product 1

HCID 11270377HCID 11270377, compoundYield 100%

Conditions

Temperature
0 °C

Procedure

To a cooled solution (0° C.) of the product of Example 16A (347 mg, 0.83 mmol) in dry THF (2 mL), was added a solution of CF3CO3H in THF (4 M; 0.21 mL, 0.83 mmol). The reaction was stirred 30 minutes at 0° C., then for 30 minutes at room temperature, and concentrated under vacuum. The residue was purified by flash chromatography (35 g silica gel, 1:5:94 NH4OH-MeOH-CH2Cl2) to afford the title compound (360 mg, 100%).

Workup

  1. waitfor 30 minutes at room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography (35 g silica gel, 1:5:94 NH4OH-MeOH-CH2Cl2)

Sources & evidence

ORD record
ord-647dbd9ee1524b45900cb37d130e9ee9
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

Loading…