Benzyl Bromide → HCID 69414732, compound

HRID 852845Notes

Reaction equation

HRID 852845 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[CH:10]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:29])[C@H:10]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:38][C:35]2[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10644345HCID 10644345, compound

Product 1

HCID 69414732HCID 69414732, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (2 g, 5 mmol) in DMF (10 mL) was added over 10 min to a slurry of NaH (240 mg 60% dispersion in mineral oil, 6 mmol) in DMF (10 mL) at 0° C. The resultant solution was stirred at this temperature for 30 min. BnBr (1.128 g, 0.785 mL, 6.5 mmol) in DMF (5 mL) was then added slowly to the solution at 0° C. and then mixture warmed to room temperature over 1.5 h. After stirring overnight the reaction was quenched and the solvent removed. The residue was taken up into EtOAc and washed with water, brine and dried with MgSO4. Filtration and removal of the solvent yielded crude material which was subject to column chromatography (silica gel, 50% EtOAc/petroleum ether, Rf 0.85) to give the ester (2.276 g, 92%). 13C NMR (CDCl3) δ 172.0, 155.2, 137.4, 136.5, 135.4, 128.7, 128.5, 128.3, 127.5, 127.4,126.9, 126.9, 126.6, 121.9, 119.4, 119.1, 109.7, 109.2, 79.7, 66.9, 54.5, 49.8, 28.3, 27.9. ISMS: 485 (M+H),

Workup

  1. customwas quenched
  2. customthe solvent removed
  3. washwashed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationFiltration and removal of the solvent
  6. customyielded crude material which

Sources & evidence

ORD record
ord-55f865bb006c43f88f276454dfe265fd
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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