Sodium Hydroxide → HCID 57069188, compound

HRID 2269360Notes

Reaction equation

HRID 2269360 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH2:12][CH2:13][CH3:14])[C@@H:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24].[OH-].[Na+].S(=O)(=O)(O)[O-:28].[Na+]>C1COCC1.CO>[C:18]1([CH2:17][CH2:16][CH2:15][C@H:10]([C@@H:11]([NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:12][CH2:13][CH3:14])[C:9]([OH:24])=[O:28])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 57209193HCID 57209193, compound

Product 1

HCID 57069188HCID 57069188, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-(3-phenyl-1-propyl)-4-propylazetidin-2-one (1.22 g, 3.69 mmol) in THF-methanol (2:1, 15 mL) is added 1 N aqueous sodium hydroxide (5.5 mL). The solution is stirred at 23° C. for 36 h, is acidified to pH 3 with saturated aqueous sodium bisulfate solution, and is extracted with two 100-mL portions of EtCOAc. The combined organics are dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide (2R,3s)-2-(3-phenyl-1-propyl)-3-(2-tetrahydropyranyloxyamino)hexanoic acid as an oil (0.93 g, 72% yield).

Workup

  1. extractionis extracted with two 100-mL portions of EtCOAc
  2. dry with materialThe combined organics are dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3da9f46c9a849d1a55b2105f25e6e99
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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