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

HRID 1488261노트

반응식

HRID 1488261 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-75a476381eff48d78dfb0ac4220e2aef
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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