Hydrochloric Acid → HCID 76179644, compound

HRID 1679221Notes

Reaction equation

HRID 1679221 reaction equation
C1(COC([S:8][CH:9]2[N:12]([C:13](=[C:18]([O:21]C(OCC3CC3)=O)[CH2:19][Br:20])[C:14]([O:16][CH3:17])=[O:15])[C:11](=[O:29])[CH:10]2[N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[SH:8][CH:9]1[N:12]([C:13](=[C:18]([OH:21])[CH2:19][Br:20])[C:14]([O:16][CH3:17])=[O:15])[C:11](=[O:29])[CH:10]1[N:30]1[C:31](=[O:40])[C:32]2=[CH:39][CH:38]=[CH:37][CH:36]=[C:33]2[C:34]1=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 53939027Methyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phthalimido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-cyclopropylmethoxycarbonyloxyethylidene)-acetate

Product 1

HCID 76179644HCID 76179644, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl α-[4-cyclopropylmethoxycarbonylthio-3-phthalimido-2-oxoazetidin-1-yl]-α-(2-bromo-1-cyclopropylmethoxycarbonyloxyethylidene)-acetate (500 mg) in methylene chloride (20 ml) is added aluminum chloride (510 mg) at once and the mixture is stirred at room temperature. After 1 hour, the mixture is poured into cold 3% hydrochloric acid (20 ml), and extracted with methylene chloride. The extract solution is washed with water, dried over magnesium sulfate, and evaporated to give methyl α-[4-mercapto-3-phthalimido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)-acetate (252 mg). Yield: 72.5%. IR:νmaxCHCl 3 1790, 1783, 1728, 1670, 1620 cm-1. NMR:δCDCl3 1.80d(11Hz)1H, 3.87s3H, 4.22+4.56AB2(10Hz)2H, 5.38dd (11; 5Hz)1H, 5.70d(5Hz)1H, 7.76m4H, 12.3s1H.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-ce9457ef630e48a3a3aa3d04677b1c09
Source dataset
uspto-grants-1978_03
Patent number
US04079181

Reaction notes

Loading…