Water → N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide

HRID 2063323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063323
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][N:23]=2)=[O:21])=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.O>ClCCl.C(OCC)(=O)C>[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][O:29][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:24][N:23]=2)=[O:21])=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67049798HCID 67049798, Verbindung

Produkt 1

HCID 86652250N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under ice cooling, methanesulfonyl chloride (71 μL, 0.92 mmol) was added to a solution of N-(4-t-butoxycarbonylaminothiophen-3-yl)-5-hydroxymethylpyridine-2-carboxylic acid amide (Reference Compound No. 3-1, 0.32 g, 0.93 mmol) and triethylamine (0.32 mL, 2.3 mmol) in anhydrous dichloromethane (20 mL), and then the reaction mixture was stirred for 2 hour. Water (0.15 L) and ethyl acetate (0.15 L) were added thereto and the whole was partitioned. The organic layer was washed with brine (0.15 L), dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give 0.36 g of the title reference compound as a yellow solid. (Yield 91%)

Aufarbeitung

  1. customthe whole was partitioned
  2. washThe organic layer was washed with brine (0.15 L)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customto give 0.36 g of the title reference compound as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-bc62ee5d7f014d85b9bd0a38d30238a0
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288380B2

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