Benzyl Bromide → HCID 53788322, compound

HRID 279260Notes

Reaction equation

HRID 279260 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>CC#N>[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

A solution of (S)-3-[N-{3-(trifluoromethyl)benzoyl}glycyl]aminopyrrolidine (0.060 mmol) in CH3CN (1.1 mL) and (piperidinomethyl)polystyrene (2.6-2.8 mmol/g, 30 mg) were added to a solution of benzyl bromide (0.050 mmol) in CH3CN (0.4 mL). The reaction mixture was stirred at 45° C. for 5 h. After the mixture was cooled to room temperature, the resin was removed by filtration and the filtrate was concentrated. The residue was resolved in CH3CN (1.0 mL) and phenyl isocyanate (0.008 mL, 0.05 mmol) was added. The mixture was stirred at room temperature for 1 h, loaded onto Varian™ SCX column, and washed with CH3OH (15 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford (S)-1-benzyl-3-[N-{3-(trifluoromethyl)benzoyl}glycyl]aminopyrrolidine (compound 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. temperatureAfter the mixture was cooled to room temperature
  2. customthe resin was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. washwashed with CH3OH (15 mL)
  6. washProduct was eluted off
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff19668b09e145ab9f5335b5fe456994
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

Loading…