Sodium Carbonate → HCID 67435258, compound

HRID 1803389Notes

Reaction equation

HRID 1803389 reaction equation
[CH3:1][S:2]([N:5]1[CH2:21][C@H:20]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[CH:11][C:10]=3[N:19]=[C:7]2[CH2:6]1)(=[O:4])=[O:3].C1C=C(Cl)C=C(C(OO)=[O:41])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:21][C@H:20]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N+:12]([O-:41])=[CH:11][C:10]=3[N:19]=[C:7]2[CH2:6]1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67435329HCID 67435329, compound

Product 1

HCID 67435258HCID 67435258, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-[(11S)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (6.16 g, 13.4 mmol) was dissolved in 110 mL of CH2Cl2 and treated with MCPBA (4.05 g, 57-86% pure material). After stirring for 1 hour, the reaction mixture was treated with 100 mL of 5% Na2CO3 solution and the layers were separated. The aqueous layer was then extracted with CH2Cl2 (2×50 mL). The combined organic layers were concentrated under reduced pressure to give tert-butyl 3-[(11S)-9-(methylsulfonyl)-5-oxido-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (6.37 g) as a golden foam.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was then extracted with CH2Cl2 (2×50 mL)
  3. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-2346d3dc326e483dbb0caf0c9b3f2216
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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