Hydrogen iodide → HCID 86747083, compound

HRID 2253919Notes

Reaction equation

HRID 2253919 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][I:5].I.CN(CCI)P(Cl)(Cl)=O.[CH3:16][C:17]1([CH3:32])[O:21][CH:20]([CH2:22][CH2:23][P:24]([Cl:31])(N(C)CCBr)=[O:25])[CH2:19][O:18]1>>[CH3:16][C:17]1([CH3:32])[O:21][CH:20]([CH2:22][CH2:23][P:24]([Cl:31])([N:2]([CH3:1])[CH2:3][CH2:4][I:5])=[O:25])[CH2:19][O:18]1

Participants

5

Reactant 4

HCID 24841Hydrogen iodideHCID 10447621HCID 10447621, compoundHCID 17138990(2-Iodoethyl)(methyl)amineHCID 86747081[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-N-methyl-N-(2-bromoethyl)phosphoramidoyl chloride

Product 1

HCID 86747083HCID 86747083, compoundYield 61%

Procedure

This compound was prepared using N-methyl-N-2-iodoethylamine.HI via N-methyl-N-(2-iodoethyl)phosphoramidic dichloride, as described for 16a (10 mmol scale). The crude product was purified by chromatography (1:4 EtOAc:hexanes) which afforded 16c as a pale yellow oil (2.50 g, 61%): Rf 0.67 (1:1 EtOAc:hexanes); 1H NMR (CDCl3) 4.27(m, 3H), 4.10(t, 1H, J=6.52 Hz), 3.59(t, 1H, J=7.38 Hz), 3.44(m, 2H), 3.26(t, 2H, J=7.56 Hz), 2.78(d, 3H, J=12.89 Hz), 2.00(dt, 2H, J=6.02 Hz), 1.38(d, 6H, J=15.48 Hz)ppm; 31P NMR (CDCl3) -8.46, -8.69 ppm (1:1 ratio of diastereomers).

Workup

  1. customThis compound was prepared
  2. customThe crude product was purified by chromatography (1:4 EtOAc:hexanes) which

Sources & evidence

ORD record
ord-a33c053cce7b4acbbb67d521c10d9766
Source dataset
uspto-grants-1993_08
Patent number
US05233031

Reaction notes

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