Sodium Iodide → HCID 53677140, compound

HRID 1757863Notes

Reaction equation

HRID 1757863 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:17])[CH:13]=[C:12]([C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:30])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[C:42]([O:48][CH2:49]Cl)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44].[I-].[Na+]>CC(C)=O>[CH3:44][C:43]([CH3:46])([CH3:45])[C:42](=[O:47])[O:48][CH2:49][O:2][C:1](=[O:3])[CH2:4][N:5]([C:10]1[CH:15]=[C:14]([C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:17])[CH:13]=[C:12]([C:29]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:30])[CH:11]=1)[CH2:6][C:7]([O:9][CH2:49][O:48][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])=[O:8]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 87885Chloromethyl pivalateHCID 19389001HCID 19389001, compound

Product 1

HCID 53677140HCID 53677140, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.1023 g (0.174 mmol) of N-(carboxymethyl)-N-[3,5-bis[(decylamino)carbonyl]phenyl]glycine, 0.12 ml (0.84 mmol) of chloromethyl pivalate, 0.07 ml (0.49 mmol) of triethylamineand 0.04 1 g of sodium iodide in 3 ml of anhydrous acetone was stirred at reflux under argon for 17 hours. The solvent was removed, NaHCO3 solution was added to the residue and the product was extracted with ethylacetate. The dried extract was concentrated to an oil and purified by chromatography on 20 g of silica gel using 50% ethyl acetate-hexane to give 0.093 g (66% yield) of N-[3,5-bis[(decylamino)carbonyl]phenyl]-N-[2-[(2,2-dimethyl-1-oxopropoxy)methoxy]-2-oxoethyl]glycine (2,2-dimethyl-1-oxopropoxy)methyl ester as a waxy solid.

Workup

  1. temperatureat reflux under argon for 17 hours
  2. customThe solvent was removed
  3. additionNaHCO3 solution was added to the residue
  4. extractionthe product was extracted with ethylacetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to an oil
  7. custompurified by chromatography on 20 g of silica gel using 50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c3028e96e5b5416389706e6a644b6c4e
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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