Benzyl chloroformate → HCID 57179522, compound

HRID 1681168Notes

Reaction equation

HRID 1681168 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)[NH:15][C:14]1=[O:24].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)[NH:15][C:14]1=[O:24])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 14844940HCID 14844940, compound

Product 1

HCID 57179522HCID 57179522, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzyl chloroformate (5.4 mL, 0.0378 mol) in methylene chloride (10 mL) was added dropwise during 0.25 hr to a stirred, cooled (ice/H2O bath) of (3S,4R)-3-amino-4-[2-(2-furyl)ethyl]azetidin-2-one (6.82 g, 0.0378 mol) and diisopropylethylamine (6.6 mL, 0.0378 mol) in methylene chloride (75 mL). Stirring was continued with cooling for 2 hr and then for 0.5 hr at ambient temperatures. The mixture was diluted with additional methylene chloride and was sequentially washed with H2O, dilute hydrochloric acid, H2O, dilute aqueous NaHCO3, H2O and saturated NaCl. The solution was dried over MgSO4 and concentrated. The residue was crystallized from ethyl acetate to afford the title compound (7.05 g, 60% yield) as an off-white solid.

Workup

  1. temperaturewith cooling for 2 hr
  2. washwas sequentially washed with H2O, dilute hydrochloric acid, H2O, dilute aqueous NaHCO3, H2O and saturated NaCl
  3. dry with materialThe solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-eff1580141d04e9a8683718358230a5f
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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