Sodium Hydroxide → Glpg-0974

HRID 408626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408626
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][N:7]([C:16]([C@@:18]1([CH3:33])[CH2:21][CH2:20][N:19]1[C:22]([C:24]1[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[S:27][CH:28]=1)=[O:23])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1.[OH-].[Na+]>CO>[S:27]1[CH:28]=[C:24]([C:22]([N:19]2[CH2:20][CH2:21][C@:18]2([CH3:33])[C:16]([N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH2:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:17])=[O:23])[C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]1=2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 705573284-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester

Produkt 1

HCID 57520598Glpg-0974Ausbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester, Intermediate 112 (25 g, 1 eq.) in 750 mL of MeOH was added aqueous NaOH (2N) (75 mL, 3 eq.). The reaction was stirred at 20° C. for 15 h. The solvent was removed under reduced pressure and the crude was partitioned between water and EtOAc. The organic layer was discarded. The aqueous layer was acidified by addition of HCl (2N) until pH=2 and thoroughly extracted three times with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid (23.7 g, yield=97%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between water and EtOAc
  3. additionThe aqueous layer was acidified by addition of HCl (2N) until pH=2
  4. extractionthoroughly extracted three times with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3e7fbe8451e243f8ab8ca292f3528aed
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759334B2

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