Benzyl Bromide → HCID 71279185, compound

HRID 1621127Notes

Reaction equation

HRID 1621127 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C.[CH3:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>CN(C=O)C>[C:25]([O:24][C:22]([N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][CH2:10][C:11]1[N:15]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26].[CH2:45]([N:15]1[C:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:12][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:14]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21899848Ethylacetate heptaneHCID 71279243HCID 71279243, compound

Product 2

HCID 71279138HCID 71279138, compoundYield 34.6%HCID 71279185HCID 71279185, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[2-bis(tert-butoxycarbonyl)aminoethyl]-3-phenyl-[1,2,4]triazole (232 mg, 597 μmol; example 22, step 1) in DMF (2.83 mL) was added sodium hydride (55%, 25 mg, 574 μmol) at 0-5° C. The resulting suspension was stirred for 30 min. Then benzylbromide (102 mg, 71 μL, 597 μmol) was added at 0-5° C. and after 45 min the ice bath was removed and stirring was continued for 1 h. The reaction mixture was extracted with ethyl acetate (40 mL) and washed with water (3×20 mL) and brine (1×20 mL). The aqueous layers were back-extracted with ethyl acetate (40 mL) and the combined organic layer was dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) to obtain 5-[2-bis(tert-butoxycarbonyl)aminoethyl]-1-benzyl-3-phenyl-[1,2,4]triazole (115 mg, 240 μmol, 73.2%, MS: M=479.3 (M+H)+) and tert-butyl 2-(1-benzyl-3-phenyl-1H-1,2,4-triazol-5-yl)ethylcarbamate (43 mg, 114 μmol, 34.6%, MS: M=379.4 (M+H)+) both as colorless oils which were combined for the next step.

Workup

  1. customwas removed
  2. stirringstirring
  3. waitwas continued for 1 h
  4. extractionThe reaction mixture was extracted with ethyl acetate (40 mL)
  5. washwashed with water (3×20 mL) and brine (1×20 mL)
  6. extractionThe aqueous layers were back-extracted with ethyl acetate (40 mL)
  7. dry with materialthe combined organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography (

Sources & evidence

ORD record
ord-0a47bf0169f44b5ea666a18e00006ece
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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