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
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
- concentrationThe reaction mixture is concentrated to dryness by evaporation in vacuo at 45°
- concentrationthe honey-like residue is concentrated by evaporation twice more
- additionafter the addition of toluene
- dissolutionThe crude product is dissolved in dichloromethane
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation
- customDrying under a high vacuum at room temperature
Sources & evidence
- ORD record
- ord-2b785da3ec484fdab5964ec4c0105929
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488140
Linked notes
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