Acetic Anhydride → HCID 90384823, compound

HRID 928672Notes

Reaction equation

HRID 928672 reaction equation
[C:1]([C:3]1[O:4][C:5]2[C:11]([C:12]3[CH:35]=[CH:34][C:15]([O:16][CH2:17][C:18]4[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=4)[C:21]([N:23]4[CH2:30][CH2:29][CH2:28][C@H:24]4[C:25]([OH:27])=[O:26])=[O:22])=[CH:14][CH:13]=3)=[CH:10][C:9]([F:36])=[C:8]([F:37])[C:6]=2[CH:7]=1)#[N:2].C([O-])(=[O:40])C.[Na+].Cl.NO.C(OC(=O)C)(=O)C>C(O)(=O)C>[F:37][C:8]1[C:6]2[CH:7]=[C:3]([CH:1]=[N:2][OH:40])[O:4][C:5]=2[C:11]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=3)[C:21]([N:23]3[CH2:30][CH2:29][CH2:28][C@H:24]3[C:25]([OH:27])=[O:26])=[O:22])=[CH:34][CH:35]=2)=[CH:10][C:9]=1[F:36]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 90385024HCID 90385024, compound

Product 1

HCID 90384823HCID 90384823, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound (20 mg, 0.04 mmol) of Example 54 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 at 60° C. for 2 hours and stirred. After that, acetic anhydride (0.026 mL, 0.28 mmol) were added to, at 100° C. for 2 hours and stirred. 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
  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-54c8560b9dd844cfa047ba29c2fb4966
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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