Sodium Carbonate → HCID 86619531, compound

HRID 1803371Notes

Reaction equation

HRID 1803371 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][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][O:16][CH2:17][C:12]3=[N:11][C:4]=1[CH:5]=[N:6]2.ClC1C=C(C=CC=1)C(OO)=[O:32].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O-:32][N+:6]1[C:7]2[C:2](=[CH:1][CH:10]=[CH:9][CH:8]=2)[C:3]2[N:13]3[C@@H:14]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:15][O:16][CH2:17][C:12]3=[N:11][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 86619530HCID 86619530, compound

Product 1

HCID 86619531HCID 86619531, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (11S)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-ylmethylcarbamate (1.62 g, 4.58 mmol) was dissolved in 40 mL of CH2Cl2 and treated with 3-chloroperoxybenzoic acid (MCPBA) (1.23 g, 77% maximum purity). After stirring for 2 hours, the reaction mixture was treated with 40 mL of 2% Na2CO3 solution and 40 mL of CH2Cl2 and the layers were separated. The aqueous layer was then extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with 10 mL of brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give tert-butyl [(11S)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methylcarbamate (1.69 g) as a crusty, off-white solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were washed with 10 mL of brine
  4. dry with materialThe organic portion was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46c7ef3ee4024927b71d1f14cb774e98
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

Loading…