Mercuric cyanide → N-[2-Methyl-5-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxymethyl)-phenyl]-3-nitrobenzamide

HRID 965130

반응식

HRID 965130 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:21])=[C:7]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:8]=1.[Hg](C#N)C#N.[C:27]([OH:30])(=[O:29])[CH3:28].[C:31]([OH:34])(=[O:33])[CH3:32].[C:35]([OH:38])(=[O:37])[CH3:36].[C:39]([OH:42])(=[O:41])[CH3:40].[C@H:43]1(Br)[O:51][C@H:50]([CH2:52]O)[C@@H:48](O)[C@H:46](O)[C@H:44]1O.[K+].[Br-]>[N+](C)([O-])=O.[Hg](Br)Br>[CH3:21][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][O:1][C@@H:43]2[O:51][C@H:50]([CH2:52][O:41][C:39](=[O:42])[CH3:40])[C@@H:48]([O:37][C:35](=[O:38])[CH3:36])[C@H:46]([O:33][C:31](=[O:34])[CH3:32])[C@H:44]2[O:29][C:27](=[O:30])[CH3:28])=[CH:8][C:7]=1[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1

참가 물질

7

반응물 4

HCID 11591Mercuric cyanideHCID 253877Potassium BromideHCID 19074226N-(5-Hydroxymethyl-2-methylphenyl)-3-nitrobenzamideHCID 86752853alpha-D-glucopyranosyl bromide tetraacetate

생성물 1

HCID 67578982N-[2-Methyl-5-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxymethyl)-phenyl]-3-nitrobenzamide수율 57.2%

시약·촉매·용매 2

HCID 24612Mercury dibromide촉매HCID 6375Nitromethane용매

실험 절차

A mixture of N-(5-hydroxymethyl-2-methylphenyl)-3-nitrobenzamide (10.0 g, 0.034 mol), HgBr2 (10.0 g, 0.041 mol), Hg(CN)2 (15.0 g, 0.058 mol), and α-D-glucopyranosyl bromide tetraacetate (17.2 g, 0.042 mol) in nitromethane (200 mL) was heated under reflux for 4 h. 2.0M KBr was added and the mixture was stirred for 30 minutes and extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3 and brine, dried (MgSO4), and concentrated to give 12.0 g (56%) of product as a brown foam; 1H NMR (DMSO-d6) δ2.00 (m, 12 H), 2.21 (s, 3 H), 4.00 (m, 2 H), 4.20 (dd, J=12.4, 5.0 Hz, 1 H), 4.58 (d, J=12.4 Hz, 1 H), 4.82 (m, 4 H), 5.27 (t, J=9.3 Hz, 1 H), 7.10 (d, J=7.8 Hz, 1 H), 7.24 (d, J=7.8 Hz, 1 H), 7.25 (s, 1 H), 7.81 (m, 1 H), 8.42 (m, 2 H), 8.80 (s, 1 H), 10.60 (s, 1 H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-233692c36e1f45f28397fc029598e4b7
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773420

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