Methanol → (+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid

HRID 2063565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063565
C[O:2][C:3](=[O:37])[CH2:4][CH:5]([C:25]1[N:26]=[C:27]([N:30]2[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]2)[S:28][CH:29]=1)[N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[C:14]([O:23][CH3:24])=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH2:8][CH2:7]1.[OH-].[Na+].CO>C1COCC1>[OH:36][CH:33]1[CH2:32][CH2:31][N:30]([C:27]2[S:28][CH:29]=[C:25]([CH:5]([N:6]3[CH2:12][CH2:11][CH2:10][N:9]([C:13]4[C:14]([O:23][CH3:24])=[CH:15][CH:16]=[C:17]5[C:22]=4[N:21]=[CH:20][CH:19]=[CH:18]5)[CH2:8][CH2:7]3)[CH2:4][C:3]([OH:37])=[O:2])[N:26]=2)[CH2:35][CH2:34]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59366202(+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid methyl ester

Produkt 1

HCID 59366189(+/-)-3-[2-(4-Hydroxy-piperidin-1-yl)-thiazol-4-yl]-3-[4-(7-methoxy-quinolin-8-yl)-[1,4]diazepan-1-yl]-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from step 1 (660 mg, 1.26 mmol) was dissolved in THF (4.20 mL) and 1 N aq. NaOH (2.52 mL, 2.52 mmol) was added, followed by MeOH (2.10 mL). The reaction was stirred at room temp for 3 h, then concentrated. The product was taken up in CH2Cl2 and water, then acidified to pH 4 with AcOH. NH4OH was added to bring the pH to 9, then the aqueous was extracted with CH2Cl2 (3×50 mL). The combined organic was dried over MgSO4, filtered, and concentrated to give the product, which was used without further purification.

Aufarbeitung

  1. concentrationconcentrated
  2. additionNH4OH was added
  3. extractionthe aqueous was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product, which
  8. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-0d14e60185074a238e7b90b57ca539fb
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288373B2

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