Hydrochloric Acid → HCID 12901822, compound

HRID 1680506Notes

Reaction equation

HRID 1680506 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7](C(OC)=O)[N:6]1[CH2:18][CH2:19][NH:20][C:21]([O:23]C(C)(C)C)=O)=[O:4].Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]2[C:21](=[O:23])[NH:20][CH2:19][CH2:18][N:6]12)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54036883HCID 54036883, compound

Product 1

HCID 12901822HCID 12901822, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3-dihydro-2-[2-[N-(1,1-dimethylethoxycarbonyl)amino]ethyl]-2H-isoindole-1,3-dicarboxylic acid dimethyl ester (1.5 g, described in Example 23), 25% hydrochloric acid (3 ml) and ethyl acetate (30 ml) is refluxed for 2 hr and evaporated. Water (20 ml) is added and the solution is extracted with chloroform. The chloroform extract is evaporated and the residue is chromatographed on silica gel using methanol-chloroform (1:49). The eluate is evaporated and the residue (0.45 g) is crystallized from dichloromethane-hexane to obtain the title compound, mp 165°-167° C.

Workup

  1. temperatureis refluxed for 2 hr
  2. customevaporated
  3. additionWater (20 ml) is added
  4. extractionthe solution is extracted with chloroform
  5. extractionThe chloroform extract
  6. customis evaporated
  7. customthe residue is chromatographed on silica gel
  8. customThe eluate is evaporated
  9. customthe residue (0.45 g) is crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a0c1b3eb0daa4353ac92191c23a3c179
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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