Sodium Bicarbonate → Methyl (2S,3S)-3-hydroxy-2-[(triphenylmethyl)amino]butanoate

HRID 1035547Notes

Reaction equation

HRID 1035547 reaction equation
C([O:9][C@@H:10]([CH3:36])[C@@H:11]([C:32]([O:34][CH3:35])=[O:33])[NH:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C1C=CC=CC=1.C[O-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:13]([NH:12][C@H:11]([C:32]([O:34][CH3:35])=[O:33])[C@H:10]([CH3:36])[OH:9])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 67156794HCID 67156794, compound

Product 1

HCID 41156311Methyl (2S,3S)-3-hydroxy-2-[(triphenylmethyl)amino]butanoateYield 61.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of the methyl O-benzoyl-N-trityl-L-allothreoninate (1.24 g, 2.59 mmol) dissolved in 15 mL of anhydrous methanol was treated with 0.1 mL of a 25% solution of sodium methoxide in methanol. The reaction mixture was stirred under N2 for 2 days. The reaction was then treated with 10 mL of saturated aqueous NaHCO3 solution and the methanol was removed under reduced pressure. The reaction mixture was then treated with 30 mL of ethyl acetate and washed successively with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give a colorless solid. Crystallization from ethyl acetate and hexanes gave methyl N-trityl-L-allothreoninate (0.60 g) as colorless crystals.

Workup

  1. customthe methanol was removed under reduced pressure
  2. additionThe reaction mixture was then treated with 30 mL of ethyl acetate
  3. washwashed successively with H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a colorless solid
  8. customCrystallization from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-e52ee3b967104a85b98b0c795468e186
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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