Succinic anhydride → HCID 86753800, compound

HRID 1417606Notes

Reaction equation

HRID 1417606 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[CH2:21][C@:20]3([CH3:34])[C@@H:22]([CH3:33])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:32])([CH3:31])[C@@H:27]([OH:30])[CH2:28][CH2:29][C@@:19]34[O:18][C:11]=2[C:12]2[CH2:13][NH:14][CH2:15][C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]2[CH2:21][C@:20]3([CH3:34])[C@@H:22]([CH3:33])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:32])([CH3:31])[C@@H:27]([OH:30])[CH2:28][CH2:29][C@@:19]34[O:18][C:11]=2[C:12]2[CH2:13][N:14]([C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:15][C:16]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 86753797HCID 86753797, compound

Product 1

HCID 86753800HCID 86753800, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Compound (33a) (38 mg, 0.08 mmol) in dry pyridine (0.4 ml) was added 16 mg (0.16 mmol) of succinic anhydride, and the mixture stirred for 1 hour at room temperature. Ice-water was added to the reaction, followed by extraction with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (silica gel 2.0 g; chloroform:methanol:water=9:1:0.1) to give 46 mg (100%) of Compound (33c).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (silica gel 2.0 g; chloroform:methanol:water=9:1:0.1)

Sources & evidence

ORD record
ord-e520b67687f24d2da7b204f040e6a13b
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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