Pyridine → (3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-(2-nitro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1698370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698370
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([C:14](=[O:34])[N:15]([CH:31]2[CH2:33][CH2:32]2)[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=2)[CH2:11][C@H:10]([NH2:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[N+:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51](Cl)(=[O:53])=[O:52])([O-:44])=[O:43]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([NH:35][S:51]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[N+:42]([O-:44])=[O:43])(=[O:52])=[O:53])[CH2:11][C@@H:12]([C:14](=[O:34])[N:15]([CH:31]2[CH2:33][CH2:32]2)[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=2)[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 69071766(3S*,5R*)-3-Amino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 69070266(3R*,5S*)-3-{Cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-5-(2-nitro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3S*,5R*)-3-Amino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester (400 mg, 0.83 mmol) in CH2Cl2 (1 mL) are added pyridine (1 mL) and o-nitrobenzenesulfonyl chloride (274 mg, 1.2 mmol) at 0° C., then the mixture is stirred at room temperature. After 20 h, the reaction mixture is quenched by H2O (30 mL) and extracted with EtOAc (100 mL). The organic layer is successively washed with 5% aqueous KHSO4, H2O, and brine, then dried over Na2SO4 and concentrated in reduced pressure. The residue is purified by silica gel column chromatography to afford the title compound as brown amorphous material. MS: 670 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 4.14 min.

Aufarbeitung

  1. customthe reaction mixture is quenched by H2O (30 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer is successively washed with 5% aqueous KHSO4, H2O, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in reduced pressure
  6. customThe residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ae351b944bb94d71b850024e954002ee
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163773B2

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