1,2-Dibromoethane → HCID 67282754, compound

HRID 1744211Notes

Reaction equation

HRID 1744211 reaction equation
[CH2:1]([O:3][CH:4]([S:24][CH2:25][CH3:26])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:23])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([OH:19])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21])[CH3:2].[Br:27][CH2:28][CH2:29]Br.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CCCCCC>CC(C)=O.O>[CH2:1]([O:3][CH:4]([S:24][CH2:25][CH3:26])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:23])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:29][CH2:28][Br:27])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21])[CH3:2]

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 18714158HCID 18714158, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 67282754HCID 67282754, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carbox-aldehyde diethylthioacetal of formula I (800 mg, 2 mmol), 1,2-dibromoethane (940 mg, 2.5 mmol) and K2CO3 (828 mg, 3 mmol) in dry acetone (40 ml) was refluxed for 48 h. After the completion of reaction as indicated by TLC, EtOAc-hexane (7:3), the reaction mixture was poured on to the water and then extracted with ethylacetate. Evaporation of the organic layer gave the crude product, which was further purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1) gave the pure (2S)-N-[4-(2-bromoethoxy)-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal of formula II.

Workup

  1. customAfter the completion of reaction
  2. extractionextracted with ethylacetate
  3. customEvaporation of the organic layer
  4. customgave the crude product, which
  5. customwas further purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1)

Sources & evidence

ORD record
ord-088e23fa9f8c417aa2309f1815aa2fb7
Source dataset
uspto-grants-2006_03
Patent number
US07015215B2

Reaction notes

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