Acetate → HCID 23039914, compound

HRID 2166472Notes

Reaction equation

HRID 2166472 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13]1([C:29]3[CH:28]=[CH:27][C:26]4[CH:30]=[C:31](O)[CH:32]=[CH:33][C:25]=4[C:24]=3[O:23][C:22]3[CH:21]=[C:20]([N:35]([CH3:37])[CH3:36])[CH:19]=[CH:18][C:17]1=3)[O:12][C:11]2=[O:38])([OH:7])=[O:6].C(OC(=O)C)(=O)C>O>[C:1]([O:4][C:31]1[CH:32]=[CH:33][C:25]2[C:24]3[O:23][C:22]4[CH:21]=[C:20]([N:35]([CH3:36])[CH3:37])[CH:19]=[CH:18][C:17]=4[C:13]4([C:14]5[C:10](=[CH:9][C:8]([C:5]([OH:7])=[O:6])=[CH:16][CH:15]=5)[C:11](=[O:38])[O:12]4)[C:29]=3[CH:28]=[CH:27][C:26]=2[CH:30]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 175AcetateHCID 7918Acetic Anhydride2×HCID 23039913HCID 23039913, compound

Product 1

HCID 23039914HCID 23039914, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To prepare the acetate from 8, 300 mg 5'-carboxy-10-dimethylamino-3-hydroxy-spiro[7H-benzo[c]xanthene-7,1'(3'H)-isobenzofuran]-3'-one was added 5 ml acetic anhydride and the solution refluxed for 2 hours. The solution was poured into water and stirred overnight to hydrolyze excess actic anhydride. The resulting solid was collected and purified by silica gel chromatography with 10% methanol with chloroform to give 0.16 g dark violet solid, Rf =0.37 with methanol:chloroform (1:9). Absorbance maxima in potassium phosphate buffer at pH 7.0 at 511 and 540 nm; extinction coefficients of 24,100 and 21,700 cm-1M-1 respectively.

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. customThe resulting solid was collected
  3. custompurified by silica gel chromatography with 10% methanol with chloroform

Sources & evidence

ORD record
ord-050995d12d674584ac8462d8d71ef0c9
Source dataset
uspto-grants-1990_07
Patent number
US04945171

Reaction notes

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