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

HRID 965130

反応式

HRID 965130 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24612Mercury dibromide触媒HCID 6375Nitromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-233692c36e1f45f28397fc029598e4b7
出典データセット
uspto-grants-1998_06
特許番号
US05773420

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