Benzyl Bromide → Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid

HRID 2223238Notes

Reaction equation

HRID 2223238 reaction equation
FC(F)(F)C(=N[Si](C)(C)C)O[Si](C)(C)C.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24]([O:28][C:29]([NH:31][C:32]1[N:37]=[CH:36][C:35]([CH2:38][CH:39]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:40][PH:41](=[O:43])[OH:42])=[CH:34][CH:33]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[CH2:16]([P:41]([CH2:40][CH:39]([CH2:38][C:35]1[CH:36]=[N:37][C:32]([NH:31][C:29]([O:28][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:30])=[CH:33][CH:34]=1)[C:44]([O:46][CH2:47][CH3:48])=[O:45])(=[O:42])[OH:43])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 94358Bis(trimethylsilyl)trifluoroacetamideHCID 178470992HCID 178470992, compound

Product 1

HCID 68804398Benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acidYield 216.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Argon was bubbled through a mixture of BSTFA (0.3 mL; 1.3 mmol), benzyl bromide (0.1 mL; 0.7 mmol), and CH2Cl2 (1.5 mL) for 10 minutes. 2-({6-[(tert-Butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropylphosphinic acid (50 mg; 0.13 mmol) was added, and the reaction mixture was refluxed under argon for 1 h. The solution was concentrated to afford 0.13 g of crude benzyl[2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-ethoxy-3-oxopropyl]phosphinic acid.

Workup

  1. temperaturethe reaction mixture was refluxed under argon for 1 h
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-580f462ef7d04ae5a04bd74bdfd421f2
Source dataset
uspto-grants-2008_05
Patent number
US07375121B2

Reaction notes

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