Sodium Iodide → HCID 19389035, compound

HRID 1110236Notes

Reaction equation

HRID 1110236 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].CN(C)[C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][C:49]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:33]1([CH2:32][O:31][C:29](=[O:30])[CH2:28][N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=2)[CH2:28][C:29](=[O:30])[O:31][CH2:41][C:50]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 4457732HCID 4457732, compound

Product 1

HCID 19389035HCID 19389035, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.5 g (0.015 mol) of 3-(octadecyloxy)benzenamine, 7.3 ml (0.046 mol) of benzyl bromoacetate, 8.2 g (0.038 mol) of 1,8-bis(dimethylamino)naphthalene, 0.64 g (4.26 mmol) of sodium iodide in 100 ml of anhydrous acetonitrile and 25 ml of anhydrous DMF was stirred at reflux under an argon atmosphere for 48 hours. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate and washed with 0.05N HCl, with saturated NaHCO3 solution dried and concentrated at reduced pressure. Purification by HPLC using 15% ethyl acetate-hexane gave, after recrystallization of the combined pure fractions from ether-hexane, 6.56 g (69% yield, mp 55°-57°) of N-[3-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Workup

  1. temperatureat reflux under an argon atmosphere for 48 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with 0.05N HCl, with saturated NaHCO3 solution
  5. customdried
  6. concentrationconcentrated at reduced pressure
  7. customPurification by HPLC
  8. customgave

Sources & evidence

ORD record
ord-7ef45fcda02847d788d525f2fb424bca
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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