2,2'-Dithiodibenzoyl chloride → [4-(2-{2-[4-(Diethoxy-phosphorylmethyl)-phenylcarbamoyl]-phenyldisulfanyl}-benzoylamino)-benzyl]phosphonic acid diethyl ester

HRID 3735Notes

Reaction equation

HRID 3735 reaction equation
[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[CH:36]=[CH:35][C:25]([CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1>ClCCl.N1C=CC=CC=1>[CH2:32]([O:31][P:27]([CH2:26][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:1](=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=[O:13])[NH:21][C:22]2[CH:36]=[CH:35][C:25]([CH2:26][P:27]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:34])=[CH:24][CH:23]=2)=[CH:36][CH:35]=1)(=[O:34])[O:28][CH2:29][CH3:30])[CH3:33]

Participants

5

Reactant 2

HCID 881642,2'-Dithiodibenzoyl chlorideHCID 88358Diethyl p-aminobenzylphosphonate

Product 1

HCID 54009664[4-(2-{2-[4-(Diethoxy-phosphorylmethyl)-phenylcarbamoyl]-phenyldisulfanyl}-benzoylamino)-benzyl]phosphonic acid diethyl esterYield 59.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and diethyl 4-aminobenzylphosphonate (2.90 g, 11.6 mmol) in 23 mL of pyridine. The reaction mixture was stirred for 3 days at 23° C. under nitrogen atmosphere. The crude product was recrystallized from acetonitrile-DMF to yield 2.60 g of the title compound, mp 237°-238° C. (dec.).

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized from acetonitrile-DMF

Sources & evidence

ORD record
ord-b9d750e19d8b4a39925f795da813a080
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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