Sodium Hydroxide → HCID 89525751, compound

HRID 1523296Notes

Reaction equation

HRID 1523296 reaction equation
[C:1]([S:5]([NH:7][C:8]1([CH:12]([CH3:17])[C:13]([O:15]C)=[O:14])[CH2:11][O:10][CH2:9]1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([S:5]([NH:7][C:8]1([CH:12]([CH3:17])[C:13]([OH:15])=[O:14])[CH2:9][O:10][CH2:11]1)=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89526456HCID 89526456, compound

Product 1

HCID 89525751HCID 89525751, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-{3-[(tert-butylsulfinyl)amino]oxetan-3-yl}propanoate (Preparation 33, 1.25 g, 4.746 mmol) was stirred in methanol (15 mL) and a 1M aqueous solution of sodium hydroxide (15 mL) for 3 hours at room temperature. The reaction was concentrated in vacuo and partitioned between diethyl ether and water. The pH of the aqueous layer was adjusted to pH3 with potassium hydrogen sulphate and extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound that was used without purification in the next step.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between diethyl ether and water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a930c2c140b4705bba9da28466dbaa4
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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