Benzyl chloroformate → HCID 57219190, compound

HRID 1591271Notes

Reaction equation

HRID 1591271 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@H:13]1[C@@H:16]([CH2:17][CH2:18][C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:15]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14]1=[O:32].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:12][C@H:13]1[C@@H:16]([CH2:17][CH2:18][C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:15]([CH2:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C:14]1=[O:32])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86745693HCID 86745693, compound

Product 1

HCID 57219190HCID 57219190, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (485 μL, 3.4 mmols) in methylene chloride (2.5 mL) was added dropwise to a stirred, cooled (ice/H2O bath) solution of (±)-t-butyl 2-[cis-3-amino-4-(2-(2-furyl)ethyl)-2-oxoazetidin-1-yl]acetate (1.0 g, 3.4 mmols) and diisopropylethylamine (592 μL, 3.4 mmols) in methylene chloride (10 mL). Stirring was continued with cooling for 0.5 hr and then for 0.33 hr at ambient temperatures. The solution was sequentially washed with 0.05M (pH 4) ammonium phosphate, H2O, dilute aqueous NaHCO3, and saturated NaCl. The solution was dried (Na2SO4) and concentrated, and the residue was chromatographed on SiO2 (50 g) with hexane-ethyl acetate (2:1). The appropriate fractions were combined and concentrated to leave a viscous oil which was crystallized from diethyl ether-hexane to afford the title compound (1.05 g, 72% yield).

Workup

  1. temperaturewith cooling for 0.5 hr
  2. washThe solution was sequentially washed with 0.05M (pH 4) ammonium phosphate, H2O, dilute aqueous NaHCO3, and saturated NaCl
  3. dry with materialThe solution was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was chromatographed on SiO2 (50 g) with hexane-ethyl acetate (2:1)
  6. concentrationconcentrated
  7. customto leave a viscous oil which
  8. customwas crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-a6f4d9dae4a848b6809fb52b7156d361
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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