Sodium Hydroxide → HCID 89525594, compound

HRID 1523297Notes

Reaction equation

HRID 1523297 reaction equation
[C:1]([S:5]([NH:7][C:8]1([CH:12]([CH2:17][CH3:18])[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]([CH2:17][CH3:18])[C:13]([OH:15])=[O:14])[CH2:9][O:10][CH2:11]1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89526418HCID 89526418, compound

Product 1

HCID 89525594HCID 89525594, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-{3-[(tert-butylsulfinyl)amino]oxetan-3-yl}butanoate (Preparation 35, 2.89 g, 10.42 mmol) was stirred in methanol (30 mL) and a 1M aqueous solution of sodium hydroxide (30 mL) for 18 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-74c0cc927200499f8021f2c2c935c730
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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