1,2-Dichloroethane → N,N'-bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}pyridine-3,5-dicarboxamide

HRID 1488261ノート

反応式

HRID 1488261 の反応式
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[C:3]([C:10]([OH:12])=O)[CH:2]=1.[O:13]([CH2:24][CH2:25][NH2:26])[C@@H:14]1[O:22][C@@H:21]([CH3:23])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]1[OH:16].[CH2:27](Cl)[CH2:28]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C@@H:14]1([O:13][CH2:24][CH2:25][NH:26][C:7]([C:5]2[CH:6]=[N:1][CH:2]=[C:3]([C:10]([NH:26][CH2:25][CH2:24][O:13][C@@H:14]3[O:22][C@@H:27]([CH3:28])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]3[OH:16])=[O:12])[CH:4]=2)=[O:9])[O:22][C@@H:21]([CH3:23])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]1[OH:16]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 103663,5-Pyridinedicarboxylic acidHCID 10954744(2R,3S,4R,5S,6S)-2-(2-Aminoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

生成物 1

HCID 117995843N,N'-bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}pyridine-3,5-dicarboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 3,5-pyridinedicarboxylic acid (311 mg, 1.861 mmol) in DMF (30 mL) at room temperature was added 2-aminoethyl α-L-fucopyranoside (2.077 g, 9.30 mmol), DMAP (568 mg, 4.65 mmol), and EDC (1784 mg, 9.30 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated. The residue was purified by flash chromatography on C18 reverse phase silica gel (300 g), eluting with AcCN in water) to give the title compound. UPLC Method B: m/e=578.31 [M+1]; Rt=0.25 min.

後処理

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography on C18 reverse phase silica gel (300 g)
  3. washeluting with AcCN in water)

出典と根拠

ORDレコード
ord-75a476381eff48d78dfb0ac4220e2aef
出典データセット
uspto-grants-2016_08
特許番号
US09427475B2

反応ノート

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