Lithium hydroxide, monohydrate → (3S*,4R*)-3-{[(2-carboxy-2-methyl-propoxycarbonyl)-cyclopropyl-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158414
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([CH:47]2[CH2:49][CH2:48]2)[C:36]([O:38][CH2:39][C:40]([C:43]([O:45]C)=[O:44])([CH3:42])[CH3:41])=[O:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([C:36]([O:38][CH2:39][C:40]([C:43]([OH:45])=[O:44])([CH3:42])[CH3:41])=[O:37])[CH:47]2[CH2:48][CH2:49]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 68616980(3S*,4R*)-3-{[Cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 68617188(3S*,4R*)-3-{[(2-carboxy-2-methyl-propoxycarbonyl)-cyclopropyl-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (3S*,4R*)-3-{[cyclopropyl-(2-methoxycarbonyl-2-methyl-propoxycarbonyl)-amino]-methyl}-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (290 mg, 0.42 mmol) and LiOH•H2O (44 mg, 1.05 mmol) in H2O (2 mL) and THF (6 mL) is stirred at RT for 3 d. After evaporation of the solvent 1N HCl is added and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the combined extracts, filtration and evaporation of the solvent affords the title compound which is used without further purification. MS (LC-MS): 578.0 [M+H-Boc]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H20/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.44 min.

Aufarbeitung

  1. customAfter evaporation of the solvent 1N HCl
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customDrying
  5. filtration(Na2SO4) of the combined extracts, filtration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fa6d1bae729043b3b4cde4e23e428a1e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

Notizen zur Reaktion

Wird geladen…