Water → HCID 67156816, compound

HRID 549175Notes

Reaction equation

HRID 549175 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:13]3[C@@H:14]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=4)[CH2:15][O:16][CH2:17][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34].O>C(Cl)Cl>[C:33]([O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C@@H:14]2[N:13]3[C:3]4[C:2]5[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=5)[N:6]=[CH:5][C:4]=4[N:11]=[C:12]3[CH2:17][O:16][CH2:15]2)=[CH:20][CH:21]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67157100HCID 67157100, compound

Product 1

HCID 67156816HCID 67156816, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(11S)-10,11-Dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-ylmethyl]phenol (2.62 g, 7.91 mmol) was suspended in 50 mL of dry CH2Cl2 and stirred under N2. The solution was treated with triethylamine (2.2 mL, 15.8 mmol) and acetic anhydride (0.89 mL, 9.45 mmol). After 18 hours, the reaction mixture was treated with 50 mL of H2O. The layers were separated, and the organic portion was washed with H2O and brine. The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4-[(11S)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-ylmethyl]phenyl acetate (2.95 g) as a white solid.

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed with H2O and brine
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-df7674bd2eb6400d96b185bb6af1657b
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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