1,2-Dichloroethane → 3-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide

HRID 279683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279683
C(Cl)CCl.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.O.[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([O:44][CH2:45][CH3:46])[C:41]([OH:43])=[O:42])=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH:47]1[CH:52]=[CH:51][C:50]([CH:53]([NH2:56])[CH2:54][OH:55])=[CH:49][CH:48]=1>ClCCl.CCCCCCC.C(OCC)(=O)C>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][C@H:40]([O:44][CH2:45][CH3:46])[C:41]([NH:56][C@H:53]([C:50]2[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=2)[CH2:54][OH:55])=[O:43])=[CH:37][CH:38]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1.[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C@@H:40]([O:44][CH2:45][CH3:46])[C:41]([NH:56][C@H:53]([C:50]2[CH:51]=[CH:52][CH:47]=[CH:48][CH:49]=2)[CH2:54][OH:55])=[O:42])=[CH:35][CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

11

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 924662-Amino-2-phenylethanolHCID 109245703-[4-(Benzyloxy)phenyl]-2-ethoxypropanoic acid

Produkt 2

HCID 111226333-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amideAusbeute 31 %HCID 117615803-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

EDC (2.03 g; 10.61 mmole), diisopropylethylamine (1.84 ml, 10.61 mmole) and HOBt×H2O (1.43 g; 10.61 mmole) were added to a solution of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid (2.92 g, 9.74 mmole) in dry dichloromethane (30 ml) on an ice-bath. After 30 minutes the ice-bath was removed and (R)-phenylglycinol (1.46 g, 10.61 mmole) was added. After stirring at room temperature overnight ethyl acetate (100 ml) was added and the solution was washed with potassium hydrogensulfate (1 M), saturated sodium bicarbonate solution, sodium carbonate solution and brine. The organic phase was dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using ethyl acetate:heptane to give 1.5 g (yield 37%) of 3-(4-benzyloxyphenyl)-(S)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide and 1.25 g (yield 31%) of 3-(4-benzyloxyphenyl)-(R)-2-ethoxy-N-(2-hydroxy-(R)-1-phenylethyl)propanoic amide.

Aufarbeitung

  1. customAfter 30 minutes the ice-bath was removed
  2. additionwas added
  3. washthe solution was washed with potassium hydrogensulfate (1 M), saturated sodium bicarbonate solution, sodium carbonate solution and brine
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-74d42c49009f43ca971d28f2a32b1c50
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362360B1

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