Hydrochloric Acid → HCID 86592155, compound

HRID 2117792Notes

Reaction equation

HRID 2117792 reaction equation
[CH2:1]([O:8][N:9]1[CH2:12][C@@H:11]([CH2:13][CH2:14][CH2:15]CC)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:19].[OH-:20].[Li+].O.Cl.[CH2:24]1[CH2:28]OCC1.O.[CH3:30]O>>[CH2:1]([O:8][NH:9][CH:12]([CH2:28][CH3:24])[CH2:11][CH2:13][C@@H:14]([CH3:15])[C:30]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 66603070HCID 66603070, compound

Product 1

HCID 86592155HCID 86592155, compound

Procedure

To a mixture of (R)-1-benzyloxy-3-pentylazetidin-2-one (0.96 g, 3.89 mmol) in a mixture of THF-H2O-MeOH (50 mL, 3:1:1 v/v) was added lithium hydroxide monohydrate (1.91 g, 38.9 mmol). After stirring at room temperature overnight, water (25 mL) was added to the mixture. The solution was acidified to pH 5˜6 with 3N aqueous HCl solution. It was extracted with EtOAc (50 mL×2). The combined organic layers were dried over MgSO4. Removal of the solvent under vacuum provided the title compound. 1H NMR (400 MHz, CHCl3) δ 9.80 (br s, 1H), 7.37 (m, 5H), 4.75 (m, 2H), 3.14 (m, 2H), 2.74 (m, 1H), 1.70 (m, 1H), 1.53 (m, 1H), 1.38-1.25 (m, 6H), 0.91 (t, J=6.8 Hz, 3H). MH+266.

Workup

  1. extractionIt was extracted with EtOAc (50 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-c38b4d4f01284c3c8031d3b2cab446b4
Source dataset
uspto-grants-2008_10
Patent number
US07442793B2

Reaction notes

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