Methyl isocyanoacetate → 5-[6-(N-benzyloxycarbonylamino)hex-1-en-2-yl]-oxazoline-4-carboxylic acid methyl ester

HRID 376108Notes

Reaction equation

HRID 376108 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[CH2:19])[CH:17]=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:26])[CH2:23][N+:24]#[C-:25]>C1(C)C=CC=CC=1.[Cu-]=O>[CH3:20][O:21][C:22]([CH:23]1[CH:17]([C:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH2:19])[O:18][CH:25]=[N:24]1)=[O:26]

Participants

5

Reactant 2

HCID 547815Methyl isocyanoacetateHCID 189915056-(N-benzyloxycarbonylamino)-2-methylene-hexanal

Product 1

HCID 539989335-[6-(N-benzyloxycarbonylamino)hex-1-en-2-yl]-oxazoline-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

4.0 g (15.3 mmol) of 6-(N-benzyloxycarbonylamino)-2-methylene-hexanal and 1.62 ml (16.8 mmol) of isocyanoacetic acid methyl ester are dissolved in 50 ml of toluene and added dropwise at 40° to a suspension of 0.12 g of 96.4% copper(I) oxide in 50 ml of toluene. The mixture is then stirred at room temperature for 2.5 hours, filtered, introduced into a column filled with 60 g of silica gel and extracted first with hexane/ethyl acetate (1:1) and then with ethyl acetate. 5-[6-(N-benzyloxycarbonylamino)hex-1-en-2-yl]-oxazoline-4-carboxylic acid methyl ester is obtained; oil.

Workup

  1. filtrationfiltered
  2. additionintroduced into a column
  3. additionfilled with 60 g of silica gel
  4. extractionextracted first with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-fdc932897fc44aa6a203f8b46f65ae16
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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