Water → HCID 22176183, compound

HRID 1797502Notes

Reaction equation

HRID 1797502 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:5]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32](Cl)(=[O:34])[CH3:33].C(=O)([O-])O.[Na+].O>C(OCC)(=O)C>[C:32]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[C:5]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 22175477HCID 22175477, compound

Product 1

HCID 22176183HCID 22176183, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-amino-3-tert-butoxycarbonylaminomethyl-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (synthesized according to the method similar to that in Example 111 (1)) (0.1 g, 0.24 mmol), acetyl chloride (38 mg, 0.48 mmol), sodium hydrogencarbonate (81 mg, 0.96 mmol), water (0.5 ml) and ethyl acetate (5 ml) was stirred at room temperature for 2 h. The reaction mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give 6-acetylamino-3-tert-butoxycarbonylaminomethyl-2-isobutyl-4-phenyl-1(2H)-isoquinolinone (80 mg, 73%) as crystals.

Workup

  1. customsynthesized
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b553abe73604470b827b575acf003481
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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