Sodium Hydroxide → HCID 66702274, compound

HRID 1803349Notes

Reaction equation

HRID 1803349 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](O)([CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[C:13]([NH:20][C:21](=[O:23])[CH3:22])[CH:12]=3)=[O:5])[CH3:2].FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>>[CH2:32]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[C:13]([NH:20][C:21](=[O:23])[CH3:22])[CH:12]=3)=[O:5])[CH3:33]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 66702115HCID 66702115, compound

Product 1

HCID 66702274HCID 66702274, compoundYield 3.5%

Procedure

Into a flask was placed compound 8f (0.3 g, 0.66 mmol) and trifluoromethanesulfonic acid (2 mL). After heating on a steam bath for 1 h the reaction was poured into 3 N NaOH and ice. The aqueous solution was extracted with CH2Cl2 and dried over sodium sulfate. The solvent was evaporated in vacuo and the resulting residue was passed through a flash column (silica gel; 90:10:1 CH2Cl2:CH3OH:NH4OH) to give 0.01 g of compound 9f. MS m/z=435 (M+1).

Workup

  1. customInto a flask was placed
  2. temperatureAfter heating on a steam bath for 1 h the reaction
  3. extractionThe aqueous solution was extracted with CH2Cl2
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d8cdb76b9ab940ce9ee7c7eff6c83f46
Source dataset
uspto-grants-2013_01
Patent number
US08350041B2

Reaction notes

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