Acetic Acid → HCID 58477386, compound

HRID 1253578Notes

Reaction equation

HRID 1253578 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH:20]=O)[CH:18]=3)[S:13][C:6]=12.CC(O)=O.[CH3:33][NH:34][CH2:35][CH2:36][OH:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][N:34]([CH3:33])[CH2:35][CH2:36][OH:37])[CH:18]=3)[S:13][C:6]=12

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 80162-(Methylamino)ethanolHCID 5049666Sodium triacetoxyborohydrideHCID 58474435HCID 58474435, compound

Product 1

HCID 58477386HCID 58477386, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of 146 (810 mg, 2.033 mmol) in DCM (40 mL) was added HOAc (0.233 mL, 4.07 mmol) and 2-(methylamino)ethanol (305 mg, 4.07 mmol), and the reaction mixture was stirred at RT for an hour. Sodium triacetoxyborohydride (1.293 g, 6.10 mmol) was added and the mixture was stirred at RT overnight. The mixture was then diluted with saturated NaHCO3 solution then solid NaHCO3 was added to neutralize the acid. The DCM layer was collected, dried over anhydrous Na2SO4, filtered and concentrated to afford title compound 147 (930 mg, 100% yield) that was used directly in the next step with no additional purification. MS (m/z)=458.50 (M+H).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe DCM layer was collected
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e1ece839763c45e2bec51334bd9ee189
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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