Mandelic Acid → HCID 178488147, Verbindung

HRID 1094742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094742
[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[N-:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].[Na+].C(N(CC)CC)C.C(O)(=O)C(C1C=CC=CC=1)O>CC(C)=O.C([C@H]([C@@H](C(OCC)=O)O)O)(OCC)=O.ClCCl.C(=O)(O)[O-].[Na+].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Komponenten

9

Edukt 3

HCID 1292Mandelic AcidHCID 8471TriethylamineHCID 178488037HCID 178488037, Verbindung

Produkt 1

HCID 178488147HCID 178488147, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11026Titanium isopropoxideKatalysatorHCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 117410Diethyl [S-(R*,R*)]-tartrateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Omeprazole sodium (500 grams) was suspended in acetone (6.0 liters) and diethyl D-tartrate (280 grams), titanium (IV) isopropoxide (325 grams) and triethylamine (410 grams) were added sequentially at a temperature of 35-40° C. L (+) mandelic acid (207 grams) was then added and further stirred for 30-60 minutes. The separated solid was filtered, washed with acetone (500 ml) and suck dried under vacuum. The wet solid thus resulting was suspended in a mixture of dichloromethane (2.0 liters) and 5% sodium bicarbonate solution (2.0 liters) and stirred for 15-30 minutes. The dichloromethane layer was separated from the resulting solution and the solvent was distilled off up to substantial completion to get the title compound in residual mass. [Weight: 180 grams, Chiral Purity: 99.93% (S-Isomer)].

Aufarbeitung

  1. filtrationThe separated solid was filtered
  2. washwashed with acetone (500 ml)
  3. customsuck dried under vacuum
  4. customThe wet solid thus resulting
  5. stirringstirred for 15-30 minutes
  6. customThe dichloromethane layer was separated from the resulting solution
  7. distillationthe solvent was distilled off up to substantial completion

Quellen und Nachweise

ORD-Eintrag
ord-105cf9353969424e8bb1775585a06fb9
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134008B2

Notizen zur Reaktion

Wird geladen…