Chlorosuccinimide → HCID 44608782, compound

HRID 1886864Notes

Reaction equation

HRID 1886864 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[N:6]2[N:5]=[CH:4][N:3]=1.[Cl:21]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Cl:21])[CH:9]=[C:10]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 25000917HCID 25000917, compound

Product 1

HCID 44608782HCID 44608782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Compound 9 (52 mg) in anhydrous DMF (2 mL) under Ar was chilled to 0° C. and treated dropwise with a solution of N-chlorosuccinimide in anhydrous DMF (27 mg in 1 mL). The mixture was warmed to RT and stirred for 1 h. The mixture was concentrated then eluted through a silica column with 0-10% MeOH:EtOAc to give Compound 12 (5.3 mg): ESI-MS m/z 407.1 ([M+H]+); 1H NMR (d6-DMSO): δ 0.83 (s, 3H); 3.60 (m, 1H); 3.70-3.74 (m, 4H); 4.74 (s, 1H); 4.84 (t, 1H, J=5.0 Hz); 4.91 (d, 1H, J=6.4 Hz); 5.36 (s, 1H); 6.86 (s, 1H); 7.83 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. washthen eluted through a silica column with 0-10% MeOH

Sources & evidence

ORD record
ord-02e5cde88d7442c888746fddb7a467de
Source dataset
uspto-grants-2013_08
Patent number
US08501699B2

Reaction notes

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