Water → HCID 54214671, compound

HRID 256591Notes

Reaction equation

HRID 256591 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[N:16]2[CH:17]=[CH:18][CH:19]=[C:15]2[C:14](=[O:20])[N:13]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[C:12]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].O>CN(C)C=O>[C:38]([O:37][C:35](=[O:36])[CH2:34][C:11]1([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[N:16]2[CH:17]=[CH:18][CH:19]=[C:15]2[C:14](=[O:20])[N:13]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[C:12]1=[O:30])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 67722372HCID 67722372, compound

Product 1

HCID 54214671HCID 54214671, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2-(3,4-dichlorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylic acid benzyl ester (9.4 g) in anhydrous dimethylformamide (40 ml) was added portionwise sodium hydride (63% dispersion in mineral oil, 0.7 g) under ice cooling, while a stream of nitrogen was passed over the mixture. The resulting mixture was stirred at 25° C. for 1 hour and thereto was added tert-butyl bromoacetate (4.3 g). The mixture was stirred at 25° C. for 15 hours, poured into water, and extracted with ethyl acetate. The extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (20:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (9.2 g, 78.0%) as colorless crystals, mp 86°-88° C.

Workup

  1. stirringThe mixture was stirred at 25° C. for 15 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. additionFractions containing the title compound
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-2e60e017f4684329b8de959c20174f19
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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