Hydrochloric Acid → HCID 86585087, compound

HRID 1760889Notes

Reaction equation

HRID 1760889 reaction equation
[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]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 1049PyridineHCID 6212Chloroform2×HCID 2734738ST50307551

Product 1

HCID 86585087HCID 86585087, compound

Procedure

[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)].

Workup

  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

Sources & evidence

ORD record
ord-c2c654a76d65450f99f8b801894b52b4
Source dataset
uspto-grants-2005_01
Patent number
US06846505B2

Reaction notes

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