Sodium Iodide → HCID 19388980, compound

HRID 1110273Notes

Reaction equation

HRID 1110273 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:16]=[C:15]([NH2:38])[CH:14]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Br[CH2:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42].CN(C)[C:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][C:61]=2N(C)C)C=CC=1.[I-].[Na+]>CN(C=O)C>[C:45]1([CH2:44][O:43][C:41](=[O:42])[CH2:40][N:38]([C:15]2[CH:16]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:18]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:5][CH2:6][CH3:7])=[O:8])[CH:14]=2)[CH2:40][C:41](=[O:42])[O:43][CH2:53][C:62]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 54481759HCID 54481759, compound

Product 1

HCID 19388980HCID 19388980, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.82 g (3.27 mmol) of [3-[3-amino-5-(octadecyloxy)phenoxy]propyl]phosphonic acid diethyl ester, 1.6 ml (9.82 mmol) of benzyl bromoacetate, 1.8 g (8.19 mmol) of 1,8-bis-(dimethylamino)naphthalene and 0.14 g (0.92 mmol) of sodium iodide in 40 ml of acetronitrile and 15 ml of DMF was stirred at reflux under argon for 48 hours. The reaction mixture was concentrated at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with 0.05N HCl, dried and concentrated a reduced pressure to an oil which was purified by HPLC using 55% ethyl acetate-hexane. This gave 2.41 g (86% yield) of N-[3-[3-(diethoxyphosphinyl)propoxy-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester as an oil. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux under argon for 48 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe extract was washed with 0.05N HCl
  5. customdried
  6. concentrationconcentrated a reduced pressure to an oil which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-059daa2a04af4b0bb0b622039eaeb184
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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