Water → Benzyl (2-oxoazetidin-3-yl)carbamate

HRID 1285103Notes

Reaction equation

HRID 1285103 reaction equation
O[N:2]1[CH2:5][CH:4]([NH:6][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:3]1=[O:17].O.[OH-].[Na+]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[C:7]([NH:6][CH:4]1[CH2:5][NH:2][C:3]1=[O:17])([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13036852HCID 13036852, compound

Product 1

HCID 12834623Benzyl (2-oxoazetidin-3-yl)carbamateYield 62.7%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 118 mg (0.5 mmole) of N-hydroxy-3-(Cbz-amino)-2-azetidinone, prepared as described by Example 3, in 10 ml of tetrahydrofuran and 10 ml of water at pH 7 was added to a flask equipped with a magnetic stirrer, a buret, and a pH electrode. The solution was maintained under nitrogen and was treated with a solution of 0.8 ml of 20% titanium trichloride by dropwise addition from a syringe. The pH of the reaction mixture was maintained at 7.0 during the addition of the TiCl3 by the addition of 3.0 N sodium hydroxide through the buret as needed. After the addition was complete the reaction mixture was stirred at room temperature for 2 hours. The pH of the reaction mixture was adjusted to 8.0, transferred to a separatory funnel and extracted with three 25 ml portions of ethyl acetate. The combined ethyl acetate was washed with 10 ml of brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was recrystallized from ethyl acetate-hexanes to give 69 mg (60%) of 3-(Cbz-amino)-2-azetidinone as a white solid melting at about 160° C. to about 161° C.

Workup

  1. customequipped with a magnetic stirrer
  2. temperatureThe solution was maintained under nitrogen
  3. additionAfter the addition
  4. customtransferred to a separatory funnel
  5. extractionextracted with three 25 ml portions of ethyl acetate
  6. washThe combined ethyl acetate was washed with 10 ml of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-487b200b8de34bd1944c92baa2e4c5a4
Source dataset
uspto-grants-1986_01
Patent number
US04565654

Reaction notes

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