Sulfuric Acid → HCID 66585041, compound

HRID 589885Notes

Reaction equation

HRID 589885 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([O:20]CC)=[O:19])[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1.[OH-].[Na+].S(=O)(=O)(O)O>C(O)C.ClCCl>[C:14]([O:13][C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2]([Br:1])=[C:3]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:4]([C:18]([OH:20])=[O:19])=[C:5]2[CH2:10]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 66584999HCID 66584999, compound

Product 1

HCID 66585041HCID 66585041, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2.41 g (5.16 mmol) of 2-tert-butyl 8-ethyl 6-bromo-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in 18 ml of ethanol are added 10.3 ml (10.3 mmol) of 1N sodium hydroxide solution and the mixture is heated at 70° C. for 2 days. The mixture is then taken up in dichloromethane and acidified by addition of 25 ml of aqueous 1N sulfuric acid. The organic phase is separated out and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure, to give a yellow solid, which is purified by chromatography on a column of 40 g of silica gel, eluting with a mixture of 4% methanol in dichloromethane, to give 1.65 g of 2-(tert-butyloxycarbonyl)-6-bromo-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid in the form of a pale yellow powder.

Workup

  1. customThe organic phase is separated out
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated off under reduced pressure
  4. customto give a yellow solid, which
  5. customis purified by chromatography on a column of 40 g of silica gel
  6. washeluting with a mixture of 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-968e3ba31c3f49ce98a004fe9e549d59
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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