Sodium Methoxide → HCID 66841883, compound

HRID 1929008Notes

Reaction equation

HRID 1929008 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([N:18]2[CH2:23][CH2:22][CH:21]([O:24]C(=O)C(C)(C)C)[CH2:20][CH2:19]2)[CH3:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([N:18]2[CH2:19][CH2:20][CH:21]([OH:24])[CH2:22][CH2:23]2)[CH3:17])[CH2:11][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 66841547HCID 66841547, compound

Product 1

HCID 66841883HCID 66841883, compound

Procedure

Ester 54 from above (1.7 g, 3.52 mmol) is treated with NaOMe (0.5M in methanol, 21 ml, 10.5 mmol) and heated under reflux for 24 hours. The solvent is then evaporated, the residue taken up in DCM and extracted with 1N-NaOH and brine. After drying and evaporation the crued is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (from 1% to 3%) to give a white powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent is then evaporated
  4. extractionextracted with 1N-NaOH and brine
  5. customAfter drying
  6. customevaporation the
  7. customcrued is purified by chromatography on silicagel
  8. customto give a white powder

Sources & evidence

ORD record
ord-8e8607be743a48a0abcd3fef6c07dc13
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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