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Sodium Iodide → N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester

HRID 1757787
Notes
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Reaction equation

HRID 1757787 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=1.Br[CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CN(C)[C:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][C:54]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:38]1([CH2:37][O:36][C:34](=[O:35])[CH2:33][N:1]([C:2]2[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=2)[CH2:33][C:34](=[O:35])[O:36][CH2:46][C:55]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389144N,N'-(5-amino-1,3-phenylene)bisdecanamide

Product 1

HCID 19389157N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl esterYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.92 g (4.45 mmol) of N,N'-(5-amino-1,3-phenylene)bisdecanamide, 10.6 ml (0.061 mol) of benzyl bromoacetate, 2.4 g (11.1 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.19 g (1.25 mmol) of sodium iodide in 50 ml of acetonitrile and 15 ml of DMF was stirred and refluxed under an argon atmosphere for 36 hours. The solvents were removed at reduced pressure and the residue was dissolved inethyl acetate. The extract was washed with 0.05N HCl, with NaHCO3 solution, dried and concentrated to a brown solid. Purification by HPLC using 25% ethyl acetate-hexane gave 0.9 g which was recrystallized from acetone-hexane to give 0.64 g (20% yield, mp 127°-129°) of N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Workup

  1. temperaturerefluxed under an argon atmosphere for 36 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved inethyl acetate
  4. washThe extract was washed with 0.05N HCl, with NaHCO3 solution
  5. customdried
  6. concentrationconcentrated to a brown solid
  7. customPurification by HPLC
  8. customgave 0.9 g which
  9. customwas recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-1ef6dfee2f6947b9ab915e59b027a1b9
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05446189

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes