HCID 58802797, compound → HCID 71091996, compound

HRID 132805Notes

Reaction equation

HRID 132805 reaction equation
[CH3:1][C:2]1([CH3:17])[O:6][C@@H:5]([C@@H:7]2[CH2:9][N:8]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][O:3]1.[F:18][C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[C:23]([F:25])[CH:24]=1>C1COCC1.CSC.[Cu](Br)Br>[F:18][C:19]1[CH:20]=[C:21]([CH2:9][C@H:7]([NH:8][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C@H:5]2[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[O:6]2)[CH:22]=[C:23]([F:25])[CH:24]=1

Participants

5

Reactant 2

HCID 58802797HCID 58802797, compoundHCID 178505930HCID 178505930, compound

Product 1

HCID 71091996HCID 71091996, compound

Reagents, catalysts & solvents 2

HCID 11403411HCID 11403411, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

BOC-Aziridine (21), copper bromide-dimethyl sulfide (0.15 eq.), and THF were cooled to −20° and (3,5-difluorophenyl)magnesium bromide (1.25 eq.) in THF was added. The reaction was allowed to warm to 200 and stir overnight. The reaction was extracted and the solvent removed to afford the crude product (26) as a syrup.

Workup

  1. temperatureto warm to 200
  2. extractionThe reaction was extracted
  3. customthe solvent removed

Sources & evidence

ORD record
ord-9f7a50fe966a4effb10fd8fb00c3f23c
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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