1,2-Dichloroethane → benzyl 6-(bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoate

HRID 1488281Notes

Reaction equation

HRID 1488281 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[O:32]([CH2:43][CH2:44][NH:45][CH2:46][CH2:47][O:48][C@@H:49]1[O:57][C@@H:56]([CH3:58])[C@@H:54]([OH:55])[C@@H:52]([OH:53])[C@@H:50]1[OH:51])[C@@H:33]1[O:41][C@@H:40]([CH3:42])[C@@H:38]([OH:39])[C@@H:36]([OH:37])[C@@H:34]1[OH:35]>CN(C=O)C>[C@@H:49]1([O:48][CH2:47][CH2:46][N:45]([CH2:44][CH2:43][O:32][C@@H:33]2[O:41][C@@H:40]([CH3:42])[C@@H:38]([OH:39])[C@@H:36]([OH:37])[C@@H:34]2[OH:35])[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:17])[O:57][C@@H:56]([CH3:58])[C@@H:54]([OH:55])[C@@H:52]([OH:53])[C@@H:50]1[OH:51]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 11075409Adipic acid monobenzyl esterHCID 1179962542-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)ethyl alpha-L-fucopyranoside

Product 1

HCID 117995946benzyl 6-(bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(benzyloxy)-6-oxohexanoic acid (40 mg, 0.169 mmol), EDC (114 mg, 0.593 mmol) and HOBt (2.59 mg, 0.017 mmol) in DMF (5 mL) at rt was added 2-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)ethyl α-L-fucopyranoside (190 mg, 0.478 mmol). After stirring for 16 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (50 g), eluting with 5-40% AcCN in water to give the title compound. UPLC Method B: m/e=616.2923 [M+1]; Rt=3.114 min. 1H NMR (CD3OD) δ 1.24 (6H, d, J=6.58), 1.72-1.64 (4H, m), 2.45 (2H, t, J=7.11), 2.53 (2H, t, J=7.32), 3.91-3.55 (17H, m), 4.78-4.75 (2H, m), 5.14 (2H, s), 7.38-7.37 (5H, m).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on C18 reverse phase silica gel (50 g)
  3. washeluting with 5-40% AcCN in water

Sources & evidence

ORD record
ord-c40e56a2f2684466913278d271b41c96
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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