Sodium Hydroxide → HCID 89525535, compound

HRID 1523298Notes

Reaction equation

HRID 1523298 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH:16]([CH3:22])[C:17]([O:19]CC)=[O:18])[CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH:16]([CH3:22])[C:17]([OH:19])=[O:18])[CH2:13][O:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89525460HCID 89525460, compound

Product 1

HCID 89525535HCID 89525535, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(3-{[(benzyloxy)carbonyl]amino}oxetan-3-yl)propanoate (Preparation 29, 43 g, 140 mmol) was stirred in methanol (200 mL) and a 1M aqueous solution of sodium hydroxide (200 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-68a76612c7e24ab19f8fb0d6179cdf13
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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