Hydrochloric Acid → (2R)-2-({N-Benzoxy-amino}methyl)-7-octenoic acid

HRID 1786113Notes

Reaction equation

HRID 1786113 reaction equation
[CH2:1]([C@@H:7]1[CH2:10][N:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:19])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[OH2:20].[OH-].[Li+].O.Cl>C1COCC1.O.CO>[CH2:12]([O:11][NH:9][CH2:10][C@@H:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])[C:8]([OH:19])=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68849452(3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone

Product 1

HCID 86621281(2R)-2-({N-Benzoxy-amino}methyl)-7-octenoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of (3R)-3-(5-hexen-1-yl)-N-benzoxy-2-azetidinone (0.39 g, 1.52 mmol) in a mixture of THF—H2O-MeOH (15 mL, 3:1:1 v/v) was added lithium hydroxide monohydrate (1.64 g, 15.2 mmol). After stirring at room temperature overnight, water (15 mL) was added to the mixture. The solution was acidified to pH 4 with 3N aqueous HCl solution. It was extracted with EtOAc (30 mL×2). The combined organic layers were dried over MgSO4. Removal of the solvent under vacuum provided the title compound. MH+278.

Workup

  1. extractionIt was extracted with EtOAc (30 mL×2)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-9b98b35cfaaa4eef88ec2032037d7d01
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

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