Hydrochloric Acid → (S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone

HRID 615310Notes

Reaction equation

HRID 615310 reaction equation
[NH2:1][C@H:2]1[CH2:5][NH:4][C:3]1=[O:6].O.[C:8]1([CH2:14][C:15](O)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>O1CCCC1>[C:8]1([CH2:14][C:15]([NH:1][C@H:2]2[CH2:5][NH:4][C:3]2=[O:6])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 999Phenylacetic AcidHCID 13019093(3S)-3-Aminoazetidin-2-one

Product 1

HCID 13212049(S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinoneYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-3-Amino-2-azetidinone (0.86 g) is suspended in 40 ml of tetrahydrofuran and 5 ml of water is added. A solution of phenylacetic acid (1.36 g) in 10 ml of tetrahydrofuran is added, followed by N-ethyl-N'-(3-dimethylamino)propylcarbodiimide, hydrochloride (1.92 g). The solution is adjusted to pH 4 by the addition of 2N hydrochloric acid and stirred for 1 hour at room temperature. The tetrahydrofuran is removed by evaporation and the remaining suspension is filtered to yield 1 g of (S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone, melting point 182° C., dec.

Workup

  1. customThe tetrahydrofuran is removed by evaporation
  2. filtrationthe remaining suspension is filtered

Sources & evidence

ORD record
ord-ea5187aa25494649bf2ba8d023fbe291
Source dataset
uspto-grants-1985_02
Patent number
US04499016

Reaction notes

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