Hydrochloric Acid → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

HRID 279801Notes

Reaction equation

HRID 279801 reaction equation
C(OCC(C)C[N:8]1[CH2:11][C@H:10]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:9]1=[O:23])(=O)C.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>CO.O>[O:23]=[C:9]1[C@@H:10]([NH:12][C:13](=[O:14])[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][NH:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 70418121HCID 70418121, compound

Product 1

HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateYield 160.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.12 g of 1-[(acetyloxy)-2-methyl(propyl)]-2-oxo-(3S)-[[(phenylmethoxy)-carbonyl]amino]azetidine in 70 ml of methanol and 7 ml of water was cooled to -15° C. and 1.33 g of potassium carbonate and 349 mg of sodium borohydride was added. The reaction mixture was stirred at -15° C. -0° C. After the reaction was complete (about 2 hours), the mixture was neutralized to pH 7 with 2N HCl and concentrated in vacuo. The concentrate was adjusted to pH 5.8, saturated with salt and extracted with ethyl acetate (3 times). The organic layer was dried and evaporated in vacuo. The residue was combined with material from a similar experiment and triturated with ether to give 3.30 g of the title compound.

Workup

  1. custom(about 2 hours)
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate (3 times)
  4. customThe organic layer was dried
  5. customevaporated in vacuo
  6. customtriturated with ether

Sources & evidence

ORD record
ord-36a699d2b80f4631ba1fb90e81301b47
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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