Triethylamine → (2R,4S)-5-biphenyl-4-yl-2-methyl-4-(2-thiophen-2-yl-acetylamino)-pentanoic acid ethyl ester

HRID 2384021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384021
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:35]([O:37][C:38](=[O:57])[C@H:39]([CH3:56])[CH2:40][C@H:41]([NH2:55])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:45][CH:44]=1)[CH3:36].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([O:37][C:38](=[O:57])[C@H:39]([CH3:56])[CH2:40][C@H:41]([NH:55][C:7](=[O:9])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:42][C:43]1[CH:44]=[CH:45][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:47][CH:48]=1)[CH3:36]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25017086(2R,4S)-4-amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride

Produkt 1

HCID 67506137(2R,4S)-5-biphenyl-4-yl-2-methyl-4-(2-thiophen-2-yl-acetylamino)-pentanoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of thiophen-2-yl-acetic acid (0.144 mmol) in DMF (5 mL) is added HATU (0.216 mmol). After stirring the mixture at room temperature for 10 minutes, (2R,4S)-4-amino-5-biphenyl-4-yl-2-methyl-pentanoic acid ethyl ester hydrochloride (0.144 mmol) and triethylamine (0.359 mmol) is added and the mixture is stirred at room temperature for 18 hours. The mixture is poured into ethyl acetate and the mixture is washed with aqueous 1M HCl and brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure to give (2R,4S)-5-biphenyl-4-yl-2-methyl-4-(2-thiophen-2-yl-acetylamino)-pentanoic acid ethyl ester which is used directly in the subsequent hydrolysis reaction.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. washthe mixture is washed with aqueous 1M HCl and brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6cd1163e8ac4da492eda3ddea1c402f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263629B2

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