Sodium Methoxide → HCID 67566233, compound

HRID 257441Notes

Reaction equation

HRID 257441 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:5]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:4]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:3]1[CH:31]([OH:38])[CH2:32][C:33](OCC)=[O:34].C[O-].[Na+]>CO>[OH:38][CH:31]1[C@H:3]2[C@@H:2]([C@@H:6]([O:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C@@H:5]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@@H:4]2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:1][C:33](=[O:34])[CH2:32]1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 86747372HCID 86747372, compound

Product 1

HCID 67566233HCID 67566233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve [1R,2S,3R,4S,5R]-2-amino-β-hydroxy-3,4,5-tris(phenylmethoxy)cyclopentanepropanoic acid, ethyl ester (140 mg, 0.269 mmol) in methanol (15 mL) and add a catalytic amount of sodium methoxide. Heat at reflux under a nitrogen atmosphere for 90 minutes, add additional sodium methoxide and continue heating at reflux for 21/2 hours. Evaporate the solvent in vacuo and partition between ethyl ether and aqueous ammonium chloride. Separate the organic phase, wash with aqueuos sodium chloride, dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as a yellow oil which solidifies on standing (122 mg).

Workup

  1. temperatureHeat
  2. temperatureat reflux under a nitrogen atmosphere for 90 minutes
  3. temperaturecontinue heating
  4. temperatureat reflux for 21/2 hours
  5. customEvaporate the solvent in vacuo
  6. custompartition between ethyl ether and aqueous ammonium chloride
  7. customSeparate the organic phase
  8. washwash with aqueuos sodium chloride
  9. dry with materialdry (MgSO4)
  10. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-4ff8169bab7a46049ef91c69f9905a6b
Source dataset
uspto-grants-1993_11
Patent number
US05262425

Reaction notes

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