Glycolic Acid → HCID 24853450, Verbindung

HRID 2065917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065917
[NH2:1][CH2:2][CH:3]([OH:30])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][C:21]([CH2:26][CH3:27])=[C:22]([CH2:24][CH3:25])[CH:23]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH2:28][CH3:29].[C:31](O)(=[O:34])[CH2:32][OH:33].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[CH2:24]([C:22]1[CH:23]=[C:18]([C:16]2[O:15][N:14]=[C:13]([C:9]3[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH:3]([OH:30])[CH2:2][NH:1][C:32](=[O:33])[CH2:31][OH:34])=[C:7]([CH2:28][CH3:29])[CH:8]=3)[N:17]=2)[CH:19]=[N:20][C:21]=1[CH2:26][CH3:27])[CH3:25]

Komponenten

7

Edukt 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59392500HCID 59392500, Verbindung

Produkt 1

HCID 24853450HCID 24853450, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (RS)-1-amino-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol (99 mg, 0.24 mmol), glycolic acid (18.5 mg, 0.244 mmol) and Hünig's base (78 mg, 0.61 mmol) in DCM (5 mL) is added PyBOP (126.7 mg, 0.24 mmol) and the mixture is stirred at rt for 30 min. The mixture is diluted with EA, washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by chromatography on prep. TLC plates eluting with DCM:MeOH 10:1 to give N—((RS)-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (90 mg) as an oil; LC-MS: tR=0.88 min, [M+1]+=469.25.

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by chromatography on prep
  6. washTLC plates eluting with DCM:MeOH 10:1

Quellen und Nachweise

ORD-Eintrag
ord-f5967a2074ae494eba2e79065fa833fd
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288554B2

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