Benzyl Bromide → HCID 53788322, compound

HRID 133561Notes

Reaction equation

HRID 133561 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)=[O:11])=[O:7].C1CCNCC1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(N=C=O)C=CC=CC=1>C(#N)C>[CH2:29]([N:15]1[CH2:16][CH2:17][C@H:13]([NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)[CH2:14]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 7672Phenyl isocyanateHCID 8082PiperidineHCID 67004890HCID 67004890, compound

Product 1

HCID 53788322HCID 53788322, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
45 °C

Procedure

An acetonitrile (1.1 mL) solution of (S)-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (0.06 mmol) and a (piperidinomethyl)polystyrene (2.6 to 2.8 mmol/g, 30 mg) were added to an acetonitrile (0.4 mL) solution of benzyl bromide (0.050 mmol). The resulting reaction mixture was stirred at 45° C. for 5 hours. The mixture solution was cooled to room temperature, and the resin was then removed by filtration to concentrate the filtrate. The resulting residue was dissolved in acetonitrile (1.0 mL), and phenyl isocyanate (0.008 mL, 0.05 mmol) was then added to the obtained solution. The mixture solution was stirred at room temperature for 1 hour, loaded onto a Varian™ SCX column and washed with methanol (15 mL). The obtained crude product was eluted with a solution of 2 M NH3 in methanol (6 mL) and concentrated to thereby provide (S)-1-benzyl-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (Compd. No. 239) (9.0 mg, 44%). The purity was determined by RPLC/MS (99%). ESI/MS m/e 406.0 (M++H, C21H22F3N3O2).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe mixture solution was cooled to room temperature
  3. customthe resin was then removed by filtration
  4. concentrationto concentrate the filtrate
  5. dissolutionThe resulting residue was dissolved in acetonitrile (1.0 mL)
  6. stirringThe mixture solution was stirred at room temperature for 1 hour
  7. washwashed with methanol (15 mL)
  8. customThe obtained crude product
  9. washwas eluted with a solution of 2 M NH3 in methanol (6 mL)
  10. concentrationconcentrated to thereby provide (S)-1-benzyl-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (Compd. No

Sources & evidence

ORD record
ord-e69112f4e928479bb1e8a3bdae0d1041
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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