Sodium Hydroxide → HCID 57152244, compound

HRID 636021Notes

Reaction equation

HRID 636021 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][C@@H:4]1[C@H:7]([CH3:8])[N:6]([O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]1=[O:16].[OH-].[Na+].S(=O)(=O)(O)[O-:21].[Na+]>COCCOC>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][NH:6][C@@H:7]([CH3:8])[C@@H:4]([CH2:3][CH:2]([CH3:17])[CH3:1])[C:5]([OH:21])=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 57123196HCID 57123196, compound

Product 1

HCID 57152244HCID 57152244, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

(3R,4S)-3-(2-Methyl-1-propyl)-4-methyl-1-(2-tetrahydropyranyloxy)azetidin-2-one (3.5 g, 14.5 mmol) in 30 mL of ethylene glycol dimethyl ether is treated with 20 mL of 2.5 M aqueous sodium hydroxide solution. The mixture is stirred at 25° C. for 16 h and is then brought to pH 3 by addition of saturated aqueous sodium bisulfate solution. The mixture is extracted with ether and the organics are dried over magnesium sulfate and concentrated under reduced pressure to give 3.2 g (84%) of (2R,3S)-3-(2-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)butanoic acid as an oil.

Workup

  1. extractionThe mixture is extracted with ether
  2. dry with materialthe organics are dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e69824f7d05041018cf74aad163baaa1
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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