Ethyl chloroformate → HCID 86736687, compound
Reaction equation
[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21].C([NH+](CC)CC)C.C(OC(Cl)=O)C.[N-:37]=[N+:38]=[N-:39].[Na+]>C(Cl)Cl.O1CCCC1.O>[CH3:1][C:2]1([CH3:23])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:20]([OH:22])=[O:21].[N-:37]=[N+:38]=[N-:39]Participants
Conditions
- Temperature
- -10 °C
Procedure
A solution of the penicillin-G triethylammonium salt thus obtainable, in a mixture of 40 ml of methylene chloride and 40 ml of tetrahydrofurane, is cooled to -10° C. and 2.9 ml of a 10 ml solution of 2 ml of chloroformic acid ethyl ester in tetrahydrofurane are slowly added, whilst stirring. The mixture is stirred for 90 minutes at -5° to 0° C., a solution of 0.395 g of sodium azide in 4 ml of water is then added, and the mixture is stirred for 30 minutes at -5° to 0° C. It is diluted with 100 ml of ice water and extracted three times with 75 ml of methylene chloride at a time; the organic extracts are washed with water, dried and evaporated at room temperature under reduced pressure. The amorphous penicillin-G azide is thus obtained, infrared absorption spectrum (in methylene chloride): characteristic bands at 3.05μ, 4.71μ, 5.62μ, 5.80μ, 5.94μ, 6.69μ and 8.50μ.
Workup
- stirringThe mixture is stirred for 90 minutes at -5° to 0° C.
- stirringthe mixture is stirred for 30 minutes at -5° to 0° C
- extractionextracted three times with 75 ml of methylene chloride at a time
- washthe organic extracts are washed with water
- customdried
- customevaporated at room temperature under reduced pressure
Sources & evidence
- ORD record
- ord-de4382ca0ecb46ac9df6e0e3c06177e6
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04172832
Reaction notes
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