2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → HCID 117996019, compound

HRID 1488256Notes

Reaction equation

HRID 1488256 reaction equation
[C@@H:1]1([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:32])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][C@@H:27]([C:29]([OH:31])=O)[NH2:28])=[O:21])[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:46]1[C:51](=[O:52])[CH2:50][CH2:49][C:47]1=O)=[N+](C)C)C.[CH2:53]([O:60][C:61](=[O:68])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][NH3+:67])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C>[C@@H:1]1([O:11][CH2:12][CH2:13][NH:46][C:51](=[O:52])[CH2:50][CH2:49][CH2:47][CH2:19][C:20]([NH:28][C@H:27]([C:29]([NH:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][C:61]([O:60][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[O:68])=[O:31])[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][C:15](=[O:32])[NH: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])=[O:21])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 117996327HCID 117996327, compoundHCID 131736855HCID 131736855, compound

Product 1

HCID 117996019HCID 117996019, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

In a 40 mL vial was added N6-[6-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoyl]-L-lysine (150 mg, 0.324 mmol) and DMF (5 mL). The solution was cooled to 0° C. To the above solution was added ML-4 (140 mg, 0.324 mmol) in DMF (2 mL) dropwise followed by the addition of TEA (45 μL, 0.324 mmol). The reaction mixture was warmed to rt and stirred for 1 h. To the resulting mixture was added TSTU (97 mg, 0.324 mmol) followed by the addition of TEA (45 μL, 0.324 mmol). The mixture was stirred at rt for 20 min. To the resulting mixture was added a solution of 6-(benzyloxy)-6-oxohexan-1-aminium 4-methylbenzenefulfonate (127 mg, 0.324 mmol) in DMF (1.0 mL). After stirring at rt for 18 hr, the mixture was concentrated. The residue was purified by flash chromatography to give the title compound. UPLC Method B: m/e=984.5469 [M+1]; Rt=3.37 min.

Workup

  1. temperatureThe reaction mixture was warmed to rt
  2. stirringThe mixture was stirred at rt for 20 min
  3. stirringAfter stirring at rt for 18 hr
  4. concentrationthe mixture was concentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3a56398feb2a43ae9ace7add17eb92f3
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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