Benzoyl chloride → tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate

HRID 1974

Reaction equation

HRID 1974 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[C:1]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 12102991Tetraethyl 5-aminopentane-1,1-bisphosphonate

Product 1

HCID 19689031tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonateYield 30.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl chloride (0.73 g, 5.0 mmol) in dichloromethane was added slowly to a solution of tetraethyl 5-aminopentane-1,1-bisphosphonate (1.50 g, 4.5 mmol) from Example 11, part A, and triethylamine (0.76 mL, 5.5 mmol) in dichloromethane at 0° C. After warming to room temperature for 30 minutes, the reaction was quenched by addition of 1N HCl (30 mL). The product was extracted into dichloromethane (2×20 mL) and the combined organic layers were washed with saturated NaHCO3 (2×15 mL), dried (Na2SO4), and concentrated in vacuo. Flash chromatography on silica gel eluting with 15% i-propanol in ethylacetate in EtOAc gave the title compound (0.64 g) as an oil.

Workup

  1. customthe reaction was quenched by addition of 1N HCl (30 mL)
  2. extractionThe product was extracted into dichloromethane (2×20 mL)
  3. washthe combined organic layers were washed with saturated NaHCO3 (2×15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18119a89941c4368a7ad288ebe54d59f
Source dataset
uspto-grants-1998_03
Patent number
US05728650

Linked notes

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