Dichloromethane → HCID 131730820, compound

HRID 1894924Notes

Reaction equation

HRID 1894924 reaction equation
O[C@:2]1([NH:27]OCC2C3C=CC=CC=3C3C2=CC=CC=3)[C@@H:8]([O:9]C(=O)C)[C@@H:7]([O:13]C(=O)C)[C@@H:6]([C:17](=C=O)[O:18]C(=O)C)[O:5][C@@:3]1([CH:24]([NH2:26])[CH3:25])[OH:4].[OH-].[Na+].C(Cl)Cl>CO>[NH2:26][CH:24]([C@:3]1([O:5][C@H:6]([CH2:17][OH:18])[C@H:7]([OH:13])[C@H:8]([OH:9])[C@H:2]1[NH2:27])[OH:4])[CH3:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 131730821HCID 131730821, compound

Product 1

HCID 131730820HCID 131730820, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 g (0.17 mmol) of 2-hydroxy-N-9-fluorenylmethoxy-carbonyl-1-aminoethyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-galactopyranose (3) as obtained above in step 3) was dissolved in 5 ml of methanol and then 13.6 ml (8 eq.) of a 1N sodium hydroxide solution were added. The reaction mixture was stirred for 1 hour and then neutralized by adding a cation exchange resin sold under the name Dowex 50WX8 by the company Sigma-Aldrich. The resin was then removed by filtration through sintered glass and the filtrate was concentrated under reduced pressure. 0.32 g (0.14 mmol) of compound (4) was then isolated by crystallization from DCM with a yield of 84%.

Workup

  1. additionby adding a cation exchange resin
  2. customThe resin was then removed by filtration through sintered glass
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f555f5244bb64f4782bb25ee8baa3dcd
Source dataset
uspto-grants-2013_08
Patent number
US08513394B2

Reaction notes

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