Acetic Anhydride → HCID 131735060, compound

HRID 928665Notes

Reaction equation

HRID 928665 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=3)[C:20]([N:22]3[CH2:29][CH2:28][CH2:27][C@H:23]3[C:24]([OH:26])=[O:25])=[O:21])=[CH:11][CH:10]=2)=[C:4]([CH:33]=O)[CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:41][OH:42].C(OC(=O)C)(=O)C>C(O)(=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=3)[C:20]([N:22]3[CH2:29][CH2:28][CH2:27][C@H:23]3[C:24]([OH:26])=[O:25])=[O:21])=[CH:11][CH:10]=2)=[C:4]([CH:33]=[N:41][OH:42])[CH:3]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 89555424HCID 89555424, compound

Product 1

HCID 131735060HCID 131735060, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The compound (20 mg, 0.043 mmol) of Example 43 was dissolved in acetic acid (5 mL), and sodium acetate (45 mg, 0.56 mmol) and hydroxylamine hydrochloride (14 mg, 0.21 mmol) were added thereto, and stirred at 60° C. for 2 hours. After that, acetic anhydride (0.026 mL, 0.28 mmol) was added thereto, and stirred at 100° C. for 2 hours. After cooling, the solvent was distilled away, and the resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1 to thus obtain the title compound.

Workup

  1. stirringstirred at 100° C. for 2 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled away
  4. customthe resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1

Sources & evidence

ORD record
ord-cd82fdecc8d2439184bede715fcde665
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

Loading…