Ammonia → HCID 178418830, compound

HRID 10578Notes

Reaction equation

HRID 10578 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[C:21]3Cl)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:27]>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[C:21]3[NH2:27])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178418993HCID 178418993, compound

Product 1

HCID 178418830HCID 178418830, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of Intermediate 130 (500 mg) in dioxane (2.5 ml) was added with 28% aqueous ammonia solution (2.5 ml) and stirred at 150° C. for 20 hours in a sealed tube. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with dioxane (6 ml), 2 N aqueous sodium hydroxide (2 ml) and di-t-butyl dicarbonate (655 mg) and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=30:1) to obtain the title compound (95.0 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with dioxane (6 ml), 2 N aqueous sodium hydroxide (2 ml) and di-t-butyl dicarbonate (655 mg)
  4. stirringstirred at room temperature for 1 hour
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=30:1)

Sources & evidence

ORD record
ord-3dfa3be4800f47328a373a2f1c6c78bb
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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