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

HRID 1008284Notes

Reaction equation

HRID 1008284 reaction equation
C[C:2]1(C)[O:6][C:5](=[O:7])[CH:4]([CH:8]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])[O:3]1.C[O-].[Na+]>CO>[CH2:9]([C@@H:8]([C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])=[O:14])[C@H:4]([OH:3])[C:5]([O:6][CH3:2])=[O:7])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 699207311-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)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-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)pentane G-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-a4ded97f8eca4a3c9bca86ffd47ef7f4
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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