Benzyl chloroformate → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

HRID 1099204Notes

Reaction equation

HRID 1099204 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O1CCOCC1.Cl>[CH2:14]([O:13][C:11]([N:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 931923-azetidinecarboxylic Acid

Product 1

HCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acidYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of azetidine-3-carboxylic acid (5.00 g, 49.5 mmol) in dioxane (325 ml) were added 1N sodium hydroxide (124 ml, 124 mmol) and benzyl chloroformate (8.44 ml, 59.3 mmol). The reaction was allowed to stir for 18 h. The reaction was diluted with 3N HCl until pH 2 was obtained. The product was extracted with EtOAc (2×), washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 0-70% methanol (0.5% acetic acid)/dichloromethane) to yield 1-[(benzyloxy)carbonyl]azetidine-3-carboxylic acid as a yellow oil (73%). 1H NMR (400 MHz, CD3OD) δ 7.37-7.26 (m, 5H), 5.08 (s, 2H), 4.18 (m, 2H), 4.11 (br s, 2H), 3.44 (m, 1H).

Workup

  1. customwas obtained
  2. extractionThe product was extracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via flash chromatography (silica, 0-70% methanol (0.5% acetic acid)/dichloromethane)

Sources & evidence

ORD record
ord-a6588294054c4ac187ea4d51b00c4e4e
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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