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Methanol → 8-[1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

HRID 1259377
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259377
[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29](C3(CC=C)CC3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:42][CH2:41]C1.[CH3:46]O.[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>O.C(Cl)(Cl)Cl.O=[Os](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29]([C:49]3([CH2:48][CH:52]([OH:51])[CH2:41][OH:42])[CH2:46][CH2:50]3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

8

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 673454828-(1-Allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 67193830
8-[1-(2,3-Dihydroxy-propyl)-cyclopropanesulfonylamino]-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

OsO4 (0.004 g, 0.00002 mol) was added to a stirred solution of 8-(1-allyl-cyclopropanesulfonylamino)-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (125 mg, 0.0002 mol) and N-methylmorpholine-N-oxide (34 mg, 0.0003 mol) in water and THF (3 mL). The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and water. The organic layer concentrated to afford 80 mg of the crude product which was used in the next step without further purification.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. concentrationThe organic layer concentrated

Quellen und Nachweise

ORD-Eintrag
ord-75cc4fdf6d7f44ca98abb531cfeca682
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466289B2

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