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

HRID 376122

Reaktionsgleichung

Reaktionsgleichung von HRID 376122
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2b785da3ec484fdab5964ec4c0105929
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488140

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