Sodium Iodide → HCID 19389152, compound

HRID 1110295Notes

Reaction equation

HRID 1110295 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([NH2:37])[CH:19]=[CH:20][C:21]=1[O: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][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[CH2:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41].CN(C)[C:52]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][C:60]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:44]1([CH2:43][O:42][C:40](=[O:41])[CH2:39][N:37]([CH2:39][C:40](=[O:41])[O:42][CH2:52][C:61]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:18]2[CH:19]=[CH:20][C:21]([O: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][CH3:36])=[C:16]([O:15][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][CH3:14])[CH:17]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19388958HCID 19388958, compound

Product 1

HCID 19389152HCID 19389152, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.8 g (5.4 mmol) of 3,4-bis(tetradecyloxy)benzenamine, 8.6 ml (54 mmol) of benzyl bromoacetate, 2.9 g (13.5 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.3 g of sodium iodide in 60 ml of acetonitrile and 10 ml of DMF was stirred under argon for 48 hours. The solvents were removed at reduced pressure and the residue was treated with water and extracted with ethyl acetate. The dried extract was concentrated and purified by HPLC using 10% ethyl acetate-hexane to give 3.2 g (73% yield, mp 52°-52°) of N-[2-oxo-2-(phenylmethoxy)ethyl]-N-[3,4-bis(tetradecyloxy)phenyl]glycine phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Workup

  1. customThe solvents were removed at reduced pressure
  2. additionthe residue was treated with water
  3. extractionextracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-0402de0418064b9796b659408fb476ea
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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