1,3-Dibromopropane → HCID 68624457, compound

HRID 1453532Notes

Reaction equation

HRID 1453532 reaction equation
[CH2:1]([O:3][CH:4]([S:26][CH2:27][CH3:28])[C@@H:5]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][N:6]1C(=O)C1C=C(OC)C(O)=CC=1[N+]([O-])=O)[CH3:2].BrCCCBr.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CCCCCC>CC(C)=O.O>[CH2:1]([O:3][CH:4]([S:26][CH2:27][CH3:28])[CH:5]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][NH:6]1)[CH3:2]

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 68624072HCID 68624072, compound

Product 1

HCID 68624457HCID 68624457, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4,4-difluoropyrrolidine 2-carboxaldehyde diethylthioacetal IV (1 mmol), 1,3-dibromopropane (0.5 mmol) and K2CO3 (3 mmol) in dry acetone (40 ml) was refluxed for 48 h. After the completion of reaction as indicated by TLC, EtOAc-hexane (6:4), the reaction mixture was poured on to the water and then extracted with ethyl acetate. 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) to give the pure 1,1′-{[(Propane-1,3diyl)dioxy]bis[2-nitro-5-methoxy-1,4-phenylene)carbonyl]}bis[4,4-difluoropyrrolidine-2-carboxaldehyde diethylthioacetal] V.

Workup

  1. customAfter the completion of reaction
  2. extractionextracted with ethyl acetate
  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-83895608f6c24f48a2bd63578e25dd9e
Source dataset
uspto-grants-2009_01
Patent number
US07476664B2

Reaction notes

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