Dichloromethane → HCID 54273954, compound

HRID 635164Notes

Reaction equation

HRID 635164 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Cl)(=[O:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+].ClCCl.CCCCCC>C(N)=O.C(OCC)(=O)C>[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[N:25]=[N+:26]=[N-:27])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 33557Sodium AzideHCID 11748878HCID 11748878, compound

Product 1

HCID 54273954HCID 54273954, compound

Reagents, catalysts & solvents 2

HCID 713FormamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 46 (950 mg) was added to a precooled solution of 1 g of sodium azide in 10 mL formamide. The mixture was stirred at room temperature for 24 hr. The reaction mixture was poured into a mixture of 50 mL of dichloromethane and 50 g of ice. The dichloromethane layer was collected and dried and the solvent was removed to give a gum. The gum was dissolved in 2 mL ethyl acetate and added dropwise to 100 mL hexane. Crystals of 2-acetamido-3,4,6-tri-O-acetyl-1-azido-1,2-dideoxy-a-D-galactopyranose 47, formed immediately and were collected by filtration (1.0 g).

Workup

  1. customThe dichloromethane layer was collected
  2. customdried
  3. customthe solvent was removed
  4. customto give a gum

Sources & evidence

ORD record
ord-c343b873f74a4821aff6425b3dcdd525
Source dataset
uspto-grants-2001_02
Patent number
US06187762B1

Reaction notes

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