HCID 70115526, compound → HCID 70116981, compound

HRID 862115Notes

Reaction equation

HRID 862115 reaction equation
[CH2:1]([N:3]([CH2:39][CH3:40])[C:4]([C@@H:6]1[C@H:11]2[CH2:12][CH2:13][N:8]([C@@H:9]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:10]2[NH:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[O:24][CH3:25])[CH2:7]1)=[O:5])[CH3:2]>CO[Na].CO>[CH2:39]([N:3]([CH2:1][CH3:2])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([C@H:9]([CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C@@H:10]2[NH:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[O:24][CH3:25])[CH2:7]1)=[O:5])[CH3:40]

Participants

3

Reactant 1

HCID 70115526HCID 70115526, compound

Product 1

HCID 70116981HCID 70116981, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 178501943HCID 178501943, compoundSolvent

Procedure

A mixture of 17 (506 mg, 0.93 mmole) and 20%-MeONa/MeOH (140 ml) was heated at reflux under a nitrogen atmosphere for 3 hours. After cooling the reaction mixture, the resulting white suspension was poured into crushed ice and extracted with CH2Cl2 (80 ml×3). The combined organic layers were washed with brine, dried over MgSO4, and concentrated down. The resulting crude solid was purified with silica-gel chromatography (CH2Cl2 :MeOH=10:1) to give 19 (0.46 g, 0.8 mmole, 92%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. additionthe resulting white suspension was poured
  5. custominto crushed ice
  6. extractionextracted with CH2Cl2 (80 ml×3)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated down
  10. customThe resulting crude solid was purified with silica-gel chromatography (CH2Cl2 :MeOH=10:1)

Sources & evidence

ORD record
ord-3336954a87a44cf291ec04689d27d488
Source dataset
uspto-grants-1998_02
Patent number
US05716965

Reaction notes

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