Hydrochloric Acid → HCID 12912011, compound

HRID 364224Notes

Reaction equation

HRID 364224 reaction equation
[CH2:1]([C:8]1[O:14][CH:13]2[CH:10]([C:11](=[O:35])[N:12]2[CH:15]([C:32]([CH3:34])=[CH2:33])[C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:36].ClCl.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(Cl)(Cl)(Cl)Cl.CC(C)=O>[CH2:1]([C:8]1[O:14][CH:13]2[CH:10]([C:11](=[O:35])[N:12]2[CH:15]([C:32]([CH2:34][Cl:36])=[CH2:33])[C:16]([O:18][CH:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 12911985HCID 12911985, compound

Product 1

HCID 12912011HCID 12912011, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

(Step 1) To a solution of diphenylmethyl 2-(3-benzyl-7-oxo-2,6-diaza-4-oxabicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-3-butenoate (4.6 g) in ethyl acetate (70 ml) are added 2.74M-solution of hydrochloric acid in ethyl acetate (3.8 ml) and 1.47M-solution of chlorine in carbon tetrachloride (12 ml), and the mixture is stirred at room temperature for 15 minutes. Then, aqueous 5% sodium thiosulfate (80 ml), sodium hydrogencarbonate (3.4 g) and acetone (240 g) are added to the reaction mixture, and the combined solution is kept at room temperature for 2.5 hours. The product is isolated by extracting with ethyl acetate, drying over sodium sulfate, and evaporating to yield diphenylmethyl 2-(3-benzyl-7-oxo-2,6-diaza-4-oxabicyclo[3.2.0]hept-2-en-6-yl)-3-chloromethyl-3-butenoate (3.33 g), mp. 82°-83° C.

Workup

  1. waitthe combined solution is kept at room temperature for 2.5 hours
  2. customThe product is isolated
  3. extractionby extracting with ethyl acetate
  4. dry with materialdrying over sodium sulfate
  5. customevaporating

Sources & evidence

ORD record
ord-acbf700ea0124e129e4825c00c9db282
Source dataset
uspto-grants-1986_08
Patent number
US04604460

Reaction notes

Loading…