2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → HCID 118002269, compound

HRID 1488307Notes

Reaction equation

HRID 1488307 reaction equation
[C@@H:1]1([O:11][CH2:12][CH2:13][N:14]([CH2:27][CH2:28][O:29][C@@H:30]2[O:38][C@@H:37]([CH3:39])[C@@H:35]([OH:36])[C@@H:33]([OH:34])[C@@H:31]2[OH:32])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:17])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[B-](F)(F)(F)F.CN(C(O[N:53]1[C:58](=[O:59])[CH2:57][CH2:56][C:54]1=[O:55])=[N+](C)C)C.CCOC(C)=O.CO.C(#N)C.O>CN(C=O)C>[C@@H:30]1([O:29][CH2:28][CH2:27][N:14]([CH2:13][CH2:12][O:11][C@@H:1]2[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]2[OH:3])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][N:53]2[C:58](=[O:59])[CH2:57][CH2:56][C:54]2=[O:55])=[O:25])=[O:17])[O:38][C@@H:37]([CH3:39])[C@@H:35]([OH:36])[C@@H:33]([OH:34])[C@@H:31]1[OH:32]

Participants

5

Reactant 3

HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 131736875HCID 131736875, compoundHCID 131736877HCID 131736877, compound

Product 1

HCID 118002269HCID 118002269, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-(2-(bis(2-[(α-L-fucopyranosyl)oxy)ethyl)amino)acetamido)hexanoic acid (20 mg, 0.037 mmol, 1.0 eq) in DMF (1 mL) was added TSTU (16.68 mg, 0.055 mmol, 1.5 eq) followed by Hunig'sBase (7.74 μl , 0.044 mmol, 1.2 eq). The reaction was stirred at rt for 1 h. TLC (4/1/1/1 EtOAc/MeOH/ACN/water) indicated no starting material left. UPLC indicated formation of pdt. Remove DMF under reduced pressure. The crude product was used without purification. UPLC Method B: m/e=666.3351 [M+1]; Rt=2.28 min.

Workup

  1. waitleft
  2. customThe crude product was used without purification

Sources & evidence

ORD record
ord-19c6feb31ac745448f57bbe343574175
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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