Hydrochloric Acid → (3S*,4R*)-4-({Isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

HRID 1158328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158328
C([O:3][C:4]([C@H:6]1[C@H:10]([CH2:11][N:12]([CH:29]([CH3:31])[CH3:30])[C:13](=[O:28])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=2)[CH2:9][N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:7]1)=[O:5])C.O[Li].O.Cl>CO.C(Cl)Cl>[C:35]([O:34][C:32]([N:8]1[CH2:9][C@@H:10]([CH2:11][N:12]([CH:29]([CH3:30])[CH3:31])[C:13](=[O:28])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=2)[C@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:33])([CH3:36])([CH3:38])[CH3:37]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68617198HCID 68617198, Verbindung

Produkt 1

HCID 59512388(3S*,4R*)-4-({Isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3S*,4R*)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.41 g, 2.63 mmol) in MeOH (25 mL) cooled at 0° C., 662 mg of LiOH.H2O is added. The reaction mixture is stirred overnight. The mixture is taken up in CH2Cl2, an aqueous HCl (5%) solution is added and the resulting mixture is extracted 3 times with CH2Cl2, dried over Na2SO4, filtered and concentrated. The crude material is used in the next step without purification. TLC, Rf (CH2Cl2/MeOH 95:5)=0.15. MS (LC-MS): 409.0 [M-H-Boc]−; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mumin): 4.96 min.

Aufarbeitung

  1. extractionthe resulting mixture is extracted 3 times with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material is used in the next step without purification
  6. customtR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mumin)
  7. custom4.96 min.

Quellen und Nachweise

ORD-Eintrag
ord-c4230eac2a5c41778681809666ec5a00
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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