Sodium Hydroxide → HCID 20637915, compound

HRID 1856644Notes

Reaction equation

HRID 1856644 reaction equation
[CH2:1]([N:5]1[CH2:21][C:20](=[O:22])[N:19]2[C@H:7]([CH2:8][C:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][C:10]=3[C@@H:18]2[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:18]2[C:10]3[NH:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:9]=3[CH2:8][C@@H:7]3[C:6](=[O:32])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:21][C:20](=[O:22])[N:19]23)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18397590HCID 18397590, compound

Product 1

HCID 20637915HCID 20637915, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 75 (1.5 g) in methanol (100 mL) was added SnCl2 ·H2O (3.06) and the resulting mixture was heated at reflux for 8 hours. The mixture was cooled to ambient temperature, poured into ice and was adjusted to pH5 with 1N NaOH. The methanol was evaporated off and the residue was basified to pH11 with 1N NaOH and extracted with EtOAc (2×150 mL). After drying over Na2SO4 and evaporation of EtOAc, the resulting yellow powder was purified by radial chromatography eluting with CH2Cl2 to give the title compound as a white powder (550 mg) m.p.: 192° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 8 hours
  3. additionpoured into ice
  4. customThe methanol was evaporated off
  5. extractionextracted with EtOAc (2×150 mL)
  6. dry with materialAfter drying over Na2SO4 and evaporation of EtOAc
  7. customthe resulting yellow powder was purified by radial chromatography
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-ef92a1e9c643489f8a2994236dbd6bd1
Source dataset
uspto-grants-2000_11
Patent number
US06143746

Reaction notes

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