Sodium Carbonate → HCID 67435444, compound

HRID 1663435Notes

Reaction equation

HRID 1663435 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][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[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:34].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O-:34][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][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[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 67992384HCID 67992384, compound

Product 1

HCID 67435444HCID 67435444, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[(11S)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (820 mg, 2.15 mmol) was dissolved in 20 mL of CH2Cl2 and treated with 3-chloroperoxybenzoic acid (648 mg, 57-86%). After stirring for 2 h, the reaction mixture was treated with 20 mL of 2% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with CH2Cl2 (3×20 mL). The combined organic layers were concentrated under reduced pressure to give tert-butyl 3-[(11S)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (850 mg) 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. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-d2f5eaed10ef493bb99e59ec12e90f03
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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