Dicyclohexylcarbodiimide → Diethyl 2-{[2-({3-chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]amino}-2-oxoethylphosphonate

HRID 1797307Notes

Reaction equation

HRID 1797307 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[O:17])=[C:12]([Cl:25])[CH:11]=1.[CH2:26]([O:28][P:29]([CH2:34][C:35](O)=[O:36])([O:31][CH2:32][CH3:33])=[O:30])[CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:25][C:12]1[CH:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][NH:1][C:35](=[O:36])[CH2:34][P:29](=[O:30])([O:31][CH2:32][CH3:33])[O:28][CH2:26][CH3:27])[CH:15]=[CH:14][C:13]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 36704(Diethoxyphosphinyl)acetic acidHCID 22174531(4-{[2-(Aminomethyl)phenyl]amino}-2-chlorophenyl)(2-methylphenyl)methanone

Product 1

HCID 22174547Diethyl 2-{[2-({3-chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]amino}-2-oxoethylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 148 (0.20 g, 0.56 mmol) was dissolved in dry DCM (1 mL) in oven dried glass ware under an argon atmosphere. Diethylphosphonoacetic acid (0.09 mL, 0.56 mmol) was added followed by dropwise addition of dicyclohexylcarbodiimide (0.13 g, 0.61 mmol dissolved in 1 mL dry DCM). The suspension was stirred at room temperature for 7 h after which it was filtered. The filtrate was diluted with 5 mL DCM and washed with 10% aqueous NaHCO3, H2O and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a slightly coloured oil.

Workup

  1. customdried glass ware under an argon atmosphere
  2. filtrationwas filtered
  3. additionThe filtrate was diluted with 5 mL DCM
  4. washwashed with 10% aqueous NaHCO3, H2O and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-896bdddcd7fd49bf8c154c1af802383f
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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