Water → HCID 59168415, compound

HRID 1444561Notes

Reaction equation

HRID 1444561 reaction equation
[OH-:1].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]([CH2:15][S:16][CH2:17][CH:18]1[CH2:20][CH2:19]1)[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].OOS([O-])=O.[K+].C(=O)(O)[O-].[Na+].[OH2:32]>>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][S:16]([CH2:17][CH:18]1[CH2:19][CH2:20]1)(=[O:32])=[O:1])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 5

HCID 962Water2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 64140719HCID 64140719, compound

Product 1

HCID 59168415HCID 59168415, compoundYield 31%

Procedure

Sodium hydroxide (2.32 g, 58 mmol) was dissolved in water (27 mL). 2-tert-Butoxycarbonylamino-3-cyclopropylmethylsulfanyl-propionic acid (7.94 g, 29 mmol) was added. A solution of Oxone™ in water (100 mL) was added slowly. The pH was adjusted to 3 by addition of sodium bicarbonate and the reaction mixture stirred for 30 minutes and extracted with ethyl acetate. The combined organic phases were washed with brine and dried with magnesium sulfate. The solvent was removed to yield 2(R)-tert-butoxycarbonylamino-3-cyclopropylmethanesulfonyl-propionic acid (4.64 g, 15 mmol, 31%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-a46630c0cf6945d59ac9e1b4652ef66e
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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