1,2-Dichloroethane → EtOAc AcCN MeOH

HRID 1488262Notes

Reaction equation

HRID 1488262 reaction equation
[O:1]([CH2:12][CH2:13][NH2:14])[C@@H:2]1[O:10][C@@H](C)[C@@H](O)[C@@H](O)[C@@H:3]1O.[CH2:15](Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:13][CH2:12][O:1][C:2]([CH3:3])=[O:10].[C:12]([C:13]#[N:14])([CH3:15])=[O:1].[CH3:2][OH:1]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 109547442-Aminoethyl alpha-l-fucopyranoside

Product 1

HCID 131736857EtOAc AcCN MeOH

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(benzyl)carbonyl]-L-glutei acid (1.1 g, 3.91 mmol) and 2-amino ethyl α-L-fucopyranoside (2.026 g, 9.78 mmol) in DMF (10 mL) was added EDC (3.00 g, 15.64 mmol) and DMAP (0.048 g, 0.391 mmol). After stirring at rt for 24 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (80 g), eluting with 100% EtOAc for 5 column volume and then isocratic EtOAc:AcCN:MeOH 6:1:1 to give the title compound. 1H NMR (CD3OD) δ 7.38-7.29 (m, 5H), 5.13-5.05 (m, 2H), 4.76 (s, 2H), 4.09 (dd, J=5.3, 8.6, 1H), 3.95-3.91 (m, 2H), 3.74-3.65 (m, 6H), 3.53-3.25 (m, 8H), 2.30 (t, J=7.5, 2H), 2.06-2.04 (m, 1H), 1.92-1.89 (m, 1H), 1.19 (d, J=6.5, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (80 g)
  3. washeluting with 100% EtOAc for 5 column volume

Sources & evidence

ORD record
ord-898a35cc7f384b32add5da09d1b826d2
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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