Acetyl chloride → HCID 89622258, compound

HRID 1500813Notes

Reaction equation

HRID 1500813 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].FC(F)(F)C(O)=O.[NH2:15][C:16]1[C:21]2=[C:22]([C:37]3[S:38][C:39]4[C:45]([O:46][CH3:47])=[CH:44][C:43]([CH3:48])=[CH:42][C:40]=4[CH:41]=3)[C:23]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])=[C:24]([CH2:25][N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[N:20]2[N:19]=[CH:18][N:17]=1.C(Cl)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.ClCCl.CO.O>[C:3]([N:29]1[CH2:28][CH2:27][N:26]([CH2:25][C:24]2[N:20]3[C:21]([C:16]([NH2:15])=[N:17][CH:18]=[N:19]3)=[C:22]([C:37]3[S:38][C:39]4[C:45]([O:46][CH3:47])=[CH:44][C:43]([CH3:48])=[CH:42][C:40]=4[CH:41]=3)[C:23]=2[CH2:32][NH:33][C:34](=[O:36])[CH3:35])[CH2:31][CH2:30]1)(=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 89622429HCID 89622429, compound

Product 1

HCID 89622258HCID 89622258, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of Example 63 (110 mg, 229 μmol) and acetyl chloride (32 μl, 458 μmol) in THF/dichloromethane (1:2, 3 ml) was treated with sodium carbonate (194 mg, 1.83 mmol) and stirred at rt overnight. Then, the mixture was diluted with methanol (2 ml) and water (1 ml) and stirred at rt for 1 h. After evaporation, the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid). Lyophilization from 1,4-dioxane and re-purification by column chromatography on silica gel (dichloromethane/methanol 50:1→100% methanol) afforded 35 mg (28% of th.) of the title compound.

Workup

  1. stirringstirred at rt for 1 h
  2. customAfter evaporation
  3. customthe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid)
  4. customLyophilization from 1,4-dioxane and re-purification by column chromatography on silica gel (dichloromethane/methanol 50:1→100% methanol)

Sources & evidence

ORD record
ord-29554e633d734af59b85f9c8418dbf11
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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