Sodium Methoxide → HCID 59908492, compound

HRID 1008287Notes

Reaction equation

HRID 1008287 reaction equation
[CH2:1]([C@@H:5]([C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:21])[C@@H:6]([O:11]C(=O)C1C=CC=CC=1)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH3:4].C[O-].[Na+]>CO>[CH2:1]([C@@H:5]([C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[O:21])[C@@H:6]([OH:11])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59908563methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)-2-(R)-benzoyloxypropionate

Product 1

HCID 59908492HCID 59908492, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)-2-(R)-benzoyloxypropionate H-2 (8.7 mmol) in methanol (25 mL) at 0° C. was added sodium methoxide (catalytic; pH adjusted to 10) and the solution stirred for 2 h. Amberlite IR-120 resin (H+ form) was added, then the solution was filtered and concentrated to afford methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)-2-(R)-hydroxypropionate H-3 (quant.).

Workup

  1. additionAmberlite IR-120 resin (H+ form) was added
  2. filtrationthe solution was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e710f25fadcc4e3f985c7d42bc4550b6
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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