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Trifluoroacetic acid → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3S*,4S*)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

HRID 1158490
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158490
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH3:25])[S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C@H:10]([CH2:26][N:27]([CH:44]([CH3:46])[CH3:45])[C:28](=[O:43])[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:44]([N:27]([CH2:26][C@H:10]1[C@H:11]([CH2:13][N:14]([CH3:25])[S:15]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:16])=[O:17])[CH2:12][NH:8][CH2:9]1)[C:28](=[O:43])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)([CH3:46])[CH3:45]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68643106(3R*,4S*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 59512513N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3S*,4S*)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3R*,4S*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (49 mg, 0.074 mmol) in 2 mL CH2Cl2, TFA (86 μL, 1.11 mmol) is added. The mixture is stirred 4 h at RT and then poured into a saturated solution of NaHCO3. The layers are separated, and the aqueous one is back-extracted twice with CH2Cl2. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 95:5) to give the title product. TLC, Rf (CH2Cl2/MeOH 9:1)=0.2. MS (LC-MS): 563.0 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.55 min.

Aufarbeitung

  1. customThe layers are separated
  2. extractionthe aqueous one is back-extracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-affd8f161e804ea7b8287be907c4ee61
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807709B2

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