Benzyl Bromide → methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate

HRID 8836Notes

Reaction equation

HRID 8836 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:8][S:9]([CH2:12][C@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH2:31]([N:8]([CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[S:9]([CH2:12][C@H:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])(=[O:10])=[O:11])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18738453methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate

Product 1

HCID 18738452methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 mL round bottom flask equipped with magnetic stir bar and N2 inlet was charged with 1.11 g of methyl 3-[N-(diphenylmethyl) aminosulfonyl]-2(R)-methylpropionate, 447 mg K2CO3, 347 mL benzyl bromide in 20 mL DMF. The reaction was stirred overnight, concentrated in vacuo and partioned between ethyl acetate and water. The organic phase was washed with brine, dried and concentrated in vacuo to 1.2 g of a clear oil. Flash chromatography on silica gel (30% ethyl acetate/hexanes) afforded 730 mg of methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate. HRMS (M+Li): calcd. 444.1821, obs 444.1865.

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stir bar and N2 inlet
  2. concentrationconcentrated in vacuo
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo to 1.2 g of a clear oil

Sources & evidence

ORD record
ord-4f361e1fb24b4f6abd016d6bd1ac7df4
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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