Sodium Hydroxide → HCID 56992436, compound

HRID 636015Notes

Reaction equation

HRID 636015 reaction equation
[CH:1]1([CH2:7][C@@H:8]2[C@H:11]([CH2:12][CH2:13][CH3:14])[N:10]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:9]2=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].S(=O)(=O)(O)[O-:26].[Na+]>O1CCOCC1.CCOCC>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][NH:10][C@@H:11]([CH2:12][CH2:13][CH3:14])[C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]([OH:22])=[O:26]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 10924924HCID 10924924, compound

Product 1

HCID 56992436HCID 56992436, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

(3R,4S)-3-Cyclohexylmethyl-4-propyl-1-(2-tetrahydropyranyloxy)azetidin-2-one (2.25 g, 7.27 mmol) is dissolved in 10 mL of 1,4-dioxane. 2.5 N Aqueous sodium hydroxide solution (8.73 mL, 21.8 mmol) is added and the reaction stirred for 18 h at 25° C. The solution is diluted with 50 mL of ether and shaken. The organic phase is discarded and the aqueous layer is acidified with solid sodium bisulfate and then extracted with two 25-mL portions of ether. The combined organic phases are dried over sodium sulfate and concentrated in vacuo giving (2R,3S)-3-(2-tetrahydropyranyloxyamino)-2-(cyclohexylmethyl)hexanoic acid as an oil (2.02 g, 85% yield).

Workup

  1. stirringshaken
  2. extractionextracted with two 25-mL portions of ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bfdd9ba60c84b08ad9b41e92169f23b
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

Loading…