1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86760931, compound

HRID 2100230Notes

Reaction equation

HRID 2100230 reaction equation
C1C[N:4]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1CCN2C(=NCCC2)CC1.[S:45]([C:49]1[CH:50]=[C:51]([O:63][CH2:64][C:65]([OH:67])=O)[C:52]2[C:57]([CH:58]=1)=[CH:56][C:55]([S:59]([OH:62])(=[O:61])=[O:60])=[CH:54][CH:53]=2)([OH:48])(=[O:47])=[O:46]>CN(C=O)C>[S:45]([C:49]1[CH:50]=[C:51]([O:63][CH2:64][C:65]([NH2:4])=[O:67])[C:52]2[C:57]([CH:58]=1)=[CH:56][C:55]([S:59]([OH:62])(=[O:61])=[O:60])=[CH:54][CH:53]=2)([OH:48])(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724699PyBOPHCID 86760932HCID 86760932, compound

Product 1

HCID 86760931HCID 86760931, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The dendrimer (DAB-Am-32; 185 mg; Mw: 3,514) dissolved in DMF (10 mL) then added PyBop (1.84 g; 2.1 eq; Mw: 520.4), followed by a solution of DBU (1 mL) and 3,6-disulfo-1-naphthoxyacetic acid (1.22 g; 2 eq; Mw: 362.3) in DMF (10 mL). The reaction mixture was left to stir overnight at R.T under N2. The solvent was removed under reduced pressure. Then purified through a sephadex (LH20) column followed by an Ion-exchange (IR120; Na+) and freeze-dried to yield SPL7320 as a white powder (402 mg, 48%).

Workup

  1. waitThe reaction mixture was left
  2. customThe solvent was removed under reduced pressure
  3. customThen purified through a sephadex (LH20) column
  4. customfreeze-dried

Sources & evidence

ORD record
ord-61b7cf51aedd478ebf66103374ca0dc4
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

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