Hydrochloric Acid → (S)-2-((3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)amino)acetic acid ethyl ester

HRID 2278784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278784
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:25][C@@H:26]5[CH2:28][O:27]5)=[C:19]([CH2:29][CH3:30])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:31][CH3:32])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:34]([O:36][C:37](=[O:40])[CH2:38][NH2:39])[CH3:35].Cl.C(=O)([O-])[O-].CCN(C(C)C)C(C)C>CO.C(Cl)Cl>[CH2:34]([O:36][C:37](=[O:40])[CH2:38][NH:39][CH2:28][C@H:26]([OH:27])[CH2:25][O:24][C:20]1[C:21]([CH3:23])=[CH:22][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[C:8]([O:31][CH3:32])[N:7]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:11]=3)[O:16][N:15]=2)=[CH:18][C:19]=1[CH2:29][CH3:30])[CH3:35]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 86702019(S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole

Produkt 1

HCID 70557560(S)-2-((3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)amino)acetic acid ethyl esterAusbeute 9,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-5-(2-cyclopentyl-6-methoxypyridin-4-yl)-3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazole (500 mg, 1.15 mmol), glycine ethylester hydrochloride (320 mg, 2.30 mmol), of which the hydrochloride was removed by filtration over a carbonate loaded silica resin prior to use, and DIPEA (0.2 mL) in methanol (3 mL) is stirred at 60° C. for 3 days. The mixture is diluted with DCM and washed with sat. aq. NaHCO3 solution. The aq. phase is extracted once with DCM. The combined org. extracts are dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. TLC using DCM:methanol 9:1 to give (S)-2-((3-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)-2-hydroxypropyl)amino)acetic acid ethyl ester (60 mg) as a white solid; LC-MS: tR=1.03 min, [M+H]+=537.29.

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3 solution
  2. extractionThe aq. phase is extracted once with DCM
  3. dry with materialextracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-5db5b03b2dda4922a09ab29511a2490f
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133179B2

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