Benzoyl chloride → HCID 15480206, compound

HRID 1937348Notes

Reaction equation

HRID 1937348 reaction equation
[NH2:1][CH2:2][P:3]([CH2:10][CH:11]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>ClCCl>[C:6]([O:5][P:3]([CH2:10][CH:11]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])([CH2:2][NH:1][C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:35])=[O:4])([CH3:8])([CH3:9])[CH3:7]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15480205HCID 15480205, compound

Product 1

HCID 15480206HCID 15480206, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-tert-butyl 2-{[(aminomethyl)-(tert-butoxy)phosphoryl]methyl}pentane-1,5-dioate (1.222 g, 3.0 mmol) and benzoyl chloride (0.46 mL, 4.0 mmol) in dichloromethane (10 mL) was added triethylamine (0.56 mL, 4.0 mmol) at 0° C., and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with dichloromethane (15 mL), washed with 1 N HCl (25 mL), dried over Na2SO4, and concentrated. The crude material was purified by silica gel chromatography (ethyl acetate/hexanes=2/1) to give 1.259 g of colorless oil (74% yield).

Workup

  1. washwashed with 1 N HCl (25 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel chromatography (ethyl acetate/hexanes=2/1)

Sources & evidence

ORD record
ord-8e3f8cbd8e8d437db04b1ad8e9edd16a
Source dataset
uspto-grants-2002_05
Patent number
US06395718B1

Reaction notes

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