Hydrochloric Acid → HCID 86585087、化合物

HRID 1760889ノート

反応式

HRID 1760889 の反応式
[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][CH:10]=[C:9](OC(C)=O)[C@@H:8]([O:16][C:17]([CH3:19])=[O:18])[C@@H:7]1[O:20][C:21]([CH3:23])=[O:22])=[O:3].N1C=CC=CC=1.Cl.C(Cl)(Cl)Cl.[OH:35][NH2:36]>>[C:17]([O:16][C@H:8]1[C@H:7]([O:20][C:21](=[O:22])[CH3:23])[C@@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[O:11][CH2:10][C:9]1=[N:36][OH:35])(=[O:18])[CH3:19]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 1049PyridineHCID 6212Chloroform2 回HCID 27347382,3,4,6-Tetra-O-acetyl-2-hydroxy-D-glucal

生成物 1

HCID 86585087HCID 86585087、化合物

実験手順

[litt=F. W. Lichtenthaler and P. Jarglis. Tetrahedron Letters 21 (1980) 1425-1428] To a solution of 2,3,4,6-tetra-O-acetyl-2-hydroxy-D-glucal (7.90 g, 23.9 mmol) in dry pyridine (40 mL, 496 mmol), HONH2, HCl (5.85 g, 84.2 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated and dissolved in CHCl3 (300 mL). The organic phase was washed with 1 M HCl (aq., 75 mL), sat. aq. NaHCO3 (75 mL) and H2O (75 mL), dried (MgSO4) and evaporated to a syrup of 2, (7.19 g, 99%). By addition of a small volume of EtOH the product crystallysed (4.43 g, 61%, mp 86-89° C.). Two recrystallisations from toluene afforded an analytical sample: mp 90-92° C.; [α]D−39.4° (c 1.3, CHCl3) [Lit. mp 89-90° C., [α]D−39.0 (c 0.4, CHCl3)].

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in CHCl3 (300 mL)
  3. washThe organic phase was washed with 1 M HCl (aq., 75 mL), sat. aq. NaHCO3 (75 mL) and H2O (75 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a syrup of 2, (7.19 g, 99%)
  6. additionBy addition of a small volume of EtOH the product
  7. customTwo recrystallisations from toluene
  8. customafforded an analytical sample

出典と根拠

ORDレコード
ord-c2c654a76d65450f99f8b801894b52b4
出典データセット
uspto-grants-2005_01
特許番号
US06846505B2

反応ノート

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