Tetrahydrofuran → 8-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-octanoic acid methyl ester

HRID 376109Notes

Reaction equation

HRID 376109 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH2:11])[O:8][CH:7]=[N:6]1)=[O:4].[O:27]1CCCC1>O.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH:6][CH:7]=[O:27])[CH:9]([OH:8])[C:10](=[CH2:11])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 539989335-[6-(N-benzyloxycarbonylamino)hex-1-en-2-yl]-oxazoline-4-carboxylic acid methyl ester

Product 1

HCID 216926188-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-octanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 962WaterSolvent

Procedure

9.4 g (26.1 mmol) of 5-[6-(N-benzyloxycarbonylamino)hex-1-en-2-yl]-oxazoline-4-carboxylic acid methyl ester are dissolved in 40 ml of tetrahydrofuran and 20 ml of water, a few drops of triethylamine are added and the mixture is heated under reflux for 18 hours. The solvent is removed under reduced pressure and the oil that remains is taken up in a total of 125 ml of methylene chloride, dried over magnesium sulfate and concentrated to dryness by evaporation. 8-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-octanoic acid methyl ester is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent is removed under reduced pressure
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-e05150a2d9aa47fe9bb66e0d8e6a812b
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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