Dichloromethane → HCID 12795697, compound

HRID 1902222Notes

Reaction equation

HRID 1902222 reaction equation
[N+]([O-])(O[CH:4]1[O:17][C@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]([O:7][C:8](=[O:10])[CH3:9])[C@H:5]1[N:23]=[N+:24]=[N-:25])=O.[Cl:27]CCl>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[C:8]([O:7][C@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[O:17][C@H:4]([Cl:27])[C@@H:5]1[N:23]=[N+:24]=[N-:25])(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 11303394HCID 11303394, compound

Product 1

HCID 12795697HCID 12795697, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

An about 1:2 mixture of the α- and β- anomers of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl nitrate (0.377 g, 1.01 mmole) was dissolved in acetonitrile (6 ml) containing tetraethylammonium chloride (0.924 g, 5.05 mmole) and the solution was left at room temperature for 48 hours. The reaction mixture was diluted with dichloromethane (25 ml), washed with water (25 ml) and dried. Evaporation of the solvent in vacuo left a syrup (0.325 g) which showed doublets with spacings of 9.0 and 3.5 Hz at δ 5.15 and 6.20 p.p.m., respectively in the p.m.r. spectrum measured in CDCl3. These signals are assigned to the β- (XXIII) and α-anomers (XXII) for 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride, respectively. Judging from the relative intensities of the signals, the product consisted of a near 10:1 mixture of the α- and β-anomers, (XXII) and (XXIII) respectively.

Workup

  1. additionAn about 1:2 mixture of the α-
  2. washwashed with water (25 ml)
  3. customdried
  4. customEvaporation of the solvent in vacuo
  5. waitleft a syrup (0.325 g) which
  6. additionthe product consisted of a near 10:1 mixture of the α- and β-anomers, (XXII) and (XXIII) respectively

Sources & evidence

ORD record
ord-5989a555de4f42aea5171916a6ab5aa1
Source dataset
uspto-grants-1982_12
Patent number
US04362720

Reaction notes

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