Sodium Iodide → (3-carbamoyl)-5-(octadecyloxy)phenyl-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester

HRID 1110264Notes

Reaction equation

HRID 1110264 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)[C:5]([NH2:7])=[O:6].Br[CH2:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].CN(C)[C:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][C:52]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:36]1([CH2:35][O:34][C:32](=[O:33])[CH2:31][N:1]([C:2]2[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]=[C:4]([C:5](=[O:6])[NH2:7])[CH:3]=2)[CH2:31][C:32](=[O:33])[O:34][CH2:44][C:53]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389096HCID 19389096, compound

Product 1

HCID 19388969(3-carbamoyl)-5-(octadecyloxy)phenyl-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl esterYield 43.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.0 g (7.4 mmol) of 3-amino-5-(octadecyloxy)benzamide, 3.6 ml (22 mmol) of benzyl bromoacetate, 4.0 g (18.5 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.3 g (2.1 mmol) of sodium iodide in 60 ml of acetonitrile and 20 ml of DMF was stirred and heated at reflux under argon for 48 hours. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with 0.05N HCl, with NaHCO3 solution, dried and concentrated at reduced pressure to a solid. Purification by HPLC using 20% ethyl acetate-toluene gave 2.24 g (43% yield, mp 112°-114°) of N-[(3-carbamoyl)-5-(octadecyloxy)phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Workup

  1. temperatureheated
  2. temperatureat reflux under argon for 48 hours
  3. customThe solvents were removed at reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe extract was washed with 0.05N HCl, with NaHCO3 solution
  6. customdried
  7. concentrationconcentrated at reduced pressure to a solid
  8. customPurification by HPLC

Sources & evidence

ORD record
ord-91b975c58ddb481e85edc92fee6c78f2
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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