p-Toluenesulfonic acid → 6-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[2-(2-hydroxyethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

HRID 1096854

Reaktionsgleichung

Reaktionsgleichung von HRID 1096854
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][C:12]([C:40]3[S:44][C:43]([O:45][CH2:46][CH2:47][O:48][Si](C(C)(C)C)(C)C)=[N:42][CH:41]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:38][CH2:37]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH:10]([CH2:11][C:12]([C:40]3[S:44][C:43]([O:45][CH2:46][CH2:47][OH:48])=[N:42][CH:41]=3)=[C:13]2[C:24](=[O:39])[N:25]([CH:36]2[CH2:37][CH2:38]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[C:28]=2[CH3:35])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 685705317-{2-[2-(tert-Butyldimethylsilanyloxy)ethoxy]thiazol-5-yl}-6-[cyclo-propyl-(3-methoxy-2-methylbenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

Produkt 1

HCID 685707976-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[2-(2-hydroxyethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A sol. of compound E7 (3.55 mmol; 2.84 g) in MeOH (35.5 mL) was treated with para-toluenesulfonic acid (3.91 mmol; 0.74 g), and the mixture was stirred at rt for 30 min. 10% aq. Na2CO3 (20 mL) was added, and the solvents were partially removed under reduced pressure. The resulting suspension was extracted with EtOAc (200 mL), washed with 10% aq. Na2CO3 (100 mL), sat. aq. NaHCO3 (100 mL), and brine (100 mL). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The product (2.46 g; 99%) was used for the next step without purification. LC-MS: tR=1.07 min; ES+: 685.50.

Aufarbeitung

  1. customthe solvents were partially removed under reduced pressure
  2. extractionThe resulting suspension was extracted with EtOAc (200 mL)
  3. washwashed with 10% aq. Na2CO3 (100 mL), sat. aq. NaHCO3 (100 mL), and brine (100 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customThe product (2.46 g; 99%) was used for the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-ffdb970482e5475aa1856b519fd08a29
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138340B2

Verknüpfte Notizen

Wird geladen…