Benzyl Bromide → HCID 23302089, compound

HRID 862780Notes

Reaction equation

HRID 862780 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:47]1[CH:52]=[CH:51][C:50]([CH2:53]Br)=[CH:49][CH:48]=1>CN(C=O)C>[C:50]1([CH2:53][N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:23][CH2:22][N:21]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:11][CH2:10][CH2:9][N:8]([CH2:53][C:50]2[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=2)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 14585891HCID 14585891, compound

Product 1

HCID 23302089HCID 23302089, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 20.0 gm (0.03 mol) of the product from Step C in 30 ml DMF and treat with 7.5 gm (0.067 mol) KtBuO and 7.96 ml (0.067 mol) BnBr, with stirring for 18 hours. Evaporate the volatiles (0.5 mm and 45° C.) and take up the resulting residue in 1400 ml of EtOAc and water-wash (2×, 500 ml). The organic layer is then dried (MgSO4) and the solvent is evaporated (in vacuo). Flash chromatography on silica gel eluted with 20% EtOAc/hexane yields 12.4 gm (50%) of desired product as a clear viscous oil. Rf is 0.42 (silica gel plates eluted with 25% EtOAc/hexane).

Workup

  1. customEvaporate the volatiles (0.5 mm and 45° C.)
  2. washwater-wash (2×, 500 ml)
  3. dry with materialThe organic layer is then dried (MgSO4)
  4. customthe solvent is evaporated (in vacuo)
  5. washFlash chromatography on silica gel eluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-d68dda6e7b37455094735e7fa0d23e3a
Source dataset
uspto-grants-1998_02
Patent number
US05719193

Reaction notes

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