Epichlorohydrin → HCID 54456275, compound

HRID 1459139Notes

Reaction equation

HRID 1459139 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH2:16][NH2:17])=[CH:8][CH:7]=1.OC1C=CC(CCNC(=O)CN[C:32](=[O:63])[C@H:33]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH:34][C:35](=[O:58])[C@H:36]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[NH:37][C:38](=[O:50])[CH2:39][NH:40][C:41](=[O:49])[C:42]2[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=2)=CC=1.[OH-].[Na+].Cl[CH2:68][CH:69]1[CH2:71][O:70]1.[OH-].C1(C[N+](C)(C)C)C=CC=CC=1>O.CO>[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH2:16][NH:17][C:32](=[O:63])[C@H:33]([CH2:59][CH:60]([CH3:61])[CH3:62])[NH:34][C:35](=[O:58])[C@H:36]([CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[NH:37][C:38](=[O:50])[CH2:39][NH:40][C:41](=[O:49])[C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:68][CH:69]3[CH2:71][O:70]3)=[CH:44][CH:43]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 53991989HCID 53991989, compoundHCID 56628515HCID 56628515, compound

Product 1

HCID 54456275HCID 54456275, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

N-(N-(N-(N-(4-(Oxlranylmethoxy)benzoyl)glycyl) phenylalanyl) leucyl) glycine N-(2-(4-(oxiranylmethoxy)phenyl)ethyl)amide. N-(N-(N-(N-(4-Hydroxybenzoyl)-glycyl)phenylalanyl)leucyl)glycine N-(2-(4-hydroxyphenyl) ethyl)amide (106 mg, 0.131 mol) was suspended in water (12 mL) containing sodium hydroxide (52.3 mg, 1.31 mmol). Chloromethyloxirane (604 mg, 6.5 mmol) in methanol (10 mL) was added, followed by phenylmethyltrimethylammonium hydroxide (40% aqueous solution, 90 mg). The solution was stirred for 48 h at 40° C. The solvent and excess reagent were evaporated under reduced pressure. The residue was dissolved in ethyl acetate and was washed with water. The solution was dried with anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure. Column chromatography (silica gel; ethyl acetate, then ethyl acetate/methanol 39:1, then ethyl acetate/methanol 19:1, then ethyl acetate/methanol 9:1) gave N-(N-(N-(N-(4-(oxiranylmethoxy)benzoyl)glycyl)phenylalanyl)leucyl)glycine N-(2-(4-(oxiranyl-methoxy)phenyl)ethyl)amide (26.5 mg, 27%).

Workup

  1. customThe solvent and excess reagent were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwas washed with water
  4. dry with materialThe solution was dried with anhydrous magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e2c2547e1ced4e6dafb13e6e0af66b5a
Source dataset
uspto-grants-1998_12
Patent number
US05853713

Reaction notes

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