Water → 10-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-decanoic acid ethyl ester

HRID 487457Notes

Reaction equation

HRID 487457 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH2:12])[O:9][CH:8]=[N:7]1)=[O:5])[CH3:2].[OH2:30]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([NH:7][CH:8]=[O:30])[CH:10]([OH:9])[C:11](=[CH2:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 149666085-[8-(N-benzyloxycarbonylamino)oct-1-en-2-yl]-oxazoline-4-carboxylic acid ethyl ester

Product 1

HCID 1496660910-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-decanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.15 g (20.25 mmol) of 5-[8-(N-benzyloxycarbonylamino)oct-1-en-2-yl]-oxazoline-4-carboxylic acid ethyl ester are heated under reflux in 40 ml of tetrahydrofuran and 20 ml of water for 4 hours with stirring. The reaction mixture is concentrated to dryness by evaporation in vacuo at 45°, and the honey-like residue is concentrated by evaporation twice more after the addition of toluene. The crude product is dissolved in dichloromethane, dried with sodium sulfate, filtered and concentrated by evaporation. Drying under a high vacuum at room temperature yields 9.03 g of 10-(N-benzyloxycarbonylamino)-2-formylamino-3-hydroxy-4-methylene-decanoic acid ethyl ester in the form of a yellowish honey.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness by evaporation in vacuo at 45°
  2. concentrationthe honey-like residue is concentrated by evaporation twice more
  3. additionafter the addition of toluene
  4. dissolutionThe crude product is dissolved in dichloromethane
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customDrying under a high vacuum at room temperature

Sources & evidence

ORD record
ord-f9c6d02cc10e4456bedf8b9288604295
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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