Bromomethylcyclopropane → HCID 59254980, compound

HRID 639512Notes

Reaction equation

HRID 639512 reaction equation
[F:1][C:2]([F:25])([F:24])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][C@H:12]3[NH:23][CH2:22][CH2:21][C@@:18]4([C:19]=2[CH:20]=1)[C@H:13]3[CH2:14][CH2:15][CH2:16][CH2:17]4)(=[O:5])=[O:4].Br[CH2:27][CH:28]1[CH2:30][CH2:29]1>C(Cl)Cl>[CH:28]1([CH2:27][N:23]2[CH2:22][CH2:21][C@@:18]34[C:19]5[CH:20]=[C:7]([O:6][S:3]([C:2]([F:1])([F:24])[F:25])(=[O:5])=[O:4])[CH:8]=[CH:9][C:10]=5[CH2:11][C@@H:12]2[C@@H:13]3[CH2:14][CH2:15][CH2:16][CH2:17]4)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 59255008HCID 59255008, compound

Product 1

HCID 59254980HCID 59254980, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 38 (50 mg, 0.13 mmol) and TEA (74 μL, 0.53 mmol) in dry CH2Cl2 (2 mL) was slowly added (bromomethyl)cyclopropane (25 μL, 0.26 mmol) at 0° C. and the mixture stirred for 5 h. Solvent was removed under reduced pressure. The crude product was purified on a silica gel column chromatography (95:5 CH2Cl2/MeOH) to give a white solid (43 mg, 77% yield): 1H NMR (300 MHz, CDCl3) 0.19˜2.10 (m, 17H); 2.31 (d, J=13.8 Hz, 1H); 2.47˜2.59 (m, 2H); 2.78˜2.88 (m, 2H); 3.30 (s, 1H); 7.02˜7.06 (m, 1H); 7.13˜7.20 (m, 2H).

Workup

  1. customat 0° C.
  2. customSolvent was removed under reduced pressure
  3. customThe crude product was purified on a silica gel column chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-63236fede6884689812a38307d4d8903
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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