Dimethylformamide → HCID 46836070, compound

HRID 2069023Notes

Reaction equation

HRID 2069023 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:38])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:37])[CH2:33][CH2:34]SC)[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O[O:47][S:48]([O-:50])=O.[K+].[CH3:52]N(C=O)C>O.CO.CC(O)=O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:38])[NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:37])[CH2:33][CH2:34][S:48]([CH3:52])(=[O:50])=[O:47])[CH:26]=3)=[CH:15][CH:14]=2)[N:7]([C:39]2[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 23707502Potassium hydroxy sulfiteHCID 58532565HCID 58532565, compound

Product 1

HCID 46836070HCID 46836070, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of the sulfide (12) (47 mg, 0.075 mmol) in DMF (0.5 mL) was added a solution of Oxone (93 mg, 0.151 mmol) in water (1 mL). After 10 min a precipitate had formed and MeOH (2 mL) was added and stirring continued for 1 hr. The mixture was diluted with a further aliquot of MeOH (2 mL) and glacial AcOH (0.5 mL) was added. The suspension was subjected to SCX capture and release and then purified by flash column chromatography (SiO2, 12 g, 2-8% MeOH in DCM, gradient elution) to afford the title compound (Example 17) (20 mg, 38%): m/z 655 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 1.27 (9H, s), 2.39 (3H, s), 2.90 (2H, t), 3.01 (3H, s), 3.43 (2H, t), 5.38 (2H, s), 6.35 (1H, s), 7.00 (1H, d), 7.27 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.56-7.65 (3H, overlapping m), 7.93 (1H, m), 8.29-8.33 (2H, overlapping m), 8.34 (1H, d), 8.58 (1H, br s), 8.79 (1H, br s), 10.72 (1H, br s).

Workup

  1. customAfter 10 min a precipitate had formed
  2. additionwas added
  3. custompurified by flash column chromatography (SiO2, 12 g, 2-8% MeOH in DCM, gradient elution)

Sources & evidence

ORD record
ord-fca7b5f28ce94da8a08b368daade0542
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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