Triethylamine → 7-Methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester
Reaction equation
[CH3:1][CH:2]1[CH:9]2[CH:5]([CH2:6][NH:7][CH2:8]2)[C:4]2[S:10][CH:11]=[CH:12][C:3]1=2.C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl>[CH2:24]([O:23][C:21]([N:7]1[CH2:6][CH:5]2[CH:9]([CH:2]([CH3:1])[C:3]3[CH:12]=[CH:11][S:10][C:4]=32)[CH2:8]1)=[O:22])[CH3:25]Participants
5
Conditions
- Temperature
- 22 °C
Procedure
A 0° C. solution of the product from step h) (258 mg, 1.19 mmol) in CH2Cl2 (6 ml) was treated with triethylamine (497 μl, 3.57 mmol) and ethyl chloroformate (227 μl, 2.38 mmol) and the reaction was warmed to 22° C. Next, the reaction mixture was extracted with CH2Cl2 (50 ml) and brine (25 ml). The combined organic layers were dried (MgSO4) and the crude product was purified by silica-gel chromatography (hexanes:EtOAc-50:50) to give the subtitle compound (204 mg, 68%). MS calculated for C13H17NO2S+H 252, observed 252.
Workup
- extractionNext, the reaction mixture was extracted with CH2Cl2 (50 ml) and brine (25 ml)
- dry with materialThe combined organic layers were dried (MgSO4)
- customthe crude product was purified by silica-gel chromatography (hexanes:EtOAc-50:50)
Sources & evidence
- ORD record
- ord-fc5c557d6f664f99ae8fb299b8c3734d
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981919B2
Reaction notes
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