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

HRID 487444Notes

Reaction equation

HRID 487444 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-51aff28dd3ab4d52b30d0736ab9e1c14
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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