Sodium Methoxide → methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)-2-(S)-hydroxypropionate

HRID 1008292Notes

Reaction equation

HRID 1008292 reaction equation
CO[C:3]1(C2C=CC=CC=2)[O:7][C:6](=[O:8])[CH:5]([CH:9]([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:15])[CH2:10][CH2:11][CH2:12][CH3:13])[O:4]1.C[O-].[Na+]>CO>[CH2:10]([C@@H:9]([C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[O:15])[C@H:5]([OH:4])[C:6]([O:7][CH3:3])=[O:8])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 865857091-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)pentane

Product 1

HCID 59908531methyl 3-(R)-n-butyl-3-[2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)-2-(S)-hydroxypropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)pentane 1-2 (5 mmol, 50%) (5 mmol) in methanol (20 mL) was added sodium methoxide (catalytic; pH adjusted to 10) and the solution stirred for 1 hour. 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-(S)-hydroxypropionate G-3 (quant.).

Workup

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

Sources & evidence

ORD record
ord-3ed119e974ba44c78b5ddeb51f0189b3
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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