Benzyl Bromide → HCID 86601638, compound

HRID 639511Notes

Reaction equation

HRID 639511 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].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH2:26]([N:23]1[CH2:22][CH2:21][C@@:18]23[C:19]4[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]=4[CH2:11][C@@H:12]1[C@@H:13]2[CH2:14][CH2:15][CH2:16][CH2:17]3)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 59255008HCID 59255008, compound

Product 1

HCID 86601638HCID 86601638, compoundYield 84.3%

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 benzyl bromide (32 μL, 0.27 mmol) at 0° C. and stirred for 5 h. Solvent was removed under reduced pressure. The crude product was purified on a silica gel column chromatography (90:5 CH2Cl2/MeOH) to give a colorless oil (51 mg, 84% yield): 1H NMR (300 MHz, CDCl3) 1.05˜1.72 (m, 9H); 1.74˜1.85 (m, 1H); 1.90˜1.94 (m, 1H); 1.96˜2.05 (m, 1H); 2.31 (d, J=13.0 Hz, 1H); 2.48˜2.52 (m, 1H); 2.88˜2.91 (m, 1H); 3.12 (d, J=18.6 Hz, 1H); 3.67 (dd, J=13.4 Hz, 2H); 7.03˜7.38 (m, 8H).

Workup

  1. customat 0° C.
  2. customSolvent was removed under reduced pressure
  3. customThe crude product was purified on a silica gel column chromatography (90:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-524ea5f7354842959c67d8ab58e5a7c9
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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