Acetonitrile → (3S,4R)-3-Formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158383

Reaktionsgleichung

Reaktionsgleichung von HRID 1158383
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:32]([CH3:34])[CH3:33])[C:15]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]([CH3:31])=[CH:22][N:23]3[CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=2)=[O:16])[C@H:10]([CH2:35][OH:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.CO.CC#N.O.CC#N>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:32]([CH3:33])[CH3:34])[C:15]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]([CH3:31])=[CH:22][N:23]3[CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:19][CH:18]=2)=[O:16])[C@H:10]([CH:35]=[O:36])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

6

Edukt 4

HCID 6342Acetonitrile2×HCID 18373917Acetonitrile--water (1/1)HCID 21226129Dichloromethane methanolHCID 68616183(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 86622388(3S,4R)-3-Formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The title compound is prepared analogously as described for the title compound under I in Scheme 5 from (3S,4R)-3-hydroxymethyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. TLC, Rf (CH2Cl2/MeOH 95:5)=0.6. tR (HPLC, C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 5.11 min.

Aufarbeitung

  1. customThe title compound is prepared analogously
  2. custom5.11 min.

Quellen und Nachweise

ORD-Eintrag
ord-caa20b2fa9614ebaa4fbd49577de7db4
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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