Methanol → 6-Methoxy-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester

HRID 395321Notes

Reaction equation

HRID 395321 reaction equation
[Na].[C:2]([O:6][C:7]([C:9]1[C:23]2[CH:22]3[CH2:24][CH:18]([CH2:19][NH:20][CH2:21]3)[C:17]=2[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](Cl)=[N:14]2)=[O:8])([CH3:5])([CH3:4])[CH3:3].[CH3:26][OH:27]>>[C:2]([O:6][C:7]([C:9]1[C:23]2[CH:22]3[CH2:24][CH:18]([CH2:19][NH:20][CH2:21]3)[C:17]=2[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([O:27][CH3:26])=[N:14]2)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 86604389HCID 86604389, compound

Product 1

HCID 866043886-Methoxy-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester

Procedure

Sodium metal (˜12 mg) was dissolved in methanol (1 mL) under nitrogen with stirring and treated with a solution of 6-chloro-5,14-diazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaen-10-carboxylic acid tert-butyl ester (118 mg, 0.33 mmol) in methanol (3 mL) and brought to reflux for 18 hours. The mixture was cooled, concentrated, treated with H2O and extracted with CH2Cl2. The organic layer was washed with saturated NaCl solution and filtered through a cotton plug then concentrated to an oil (165 mg). (TLC: 5% methanol/CH2Cl2 Rf 0.55).

Workup

  1. temperatureto reflux for 18 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. additiontreated with H2O
  5. extractionextracted with CH2Cl2
  6. washThe organic layer was washed with saturated NaCl solution
  7. filtrationfiltered through a cotton plug
  8. concentrationthen concentrated to an oil (165 mg)

Sources & evidence

ORD record
ord-e283570c46ab498fb189d2d9a888218f
Source dataset
uspto-grants-2003_08
Patent number
US06605610B1

Reaction notes

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