Triethylamine → 3b,4,6,7,7a,8-Hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester
Reaction equation
[S:1]1[C:5]2[CH2:6][CH:7]3[CH:12]([C:4]=2[CH:3]=[CH:2]1)[CH2:11][NH:10][CH2:9][CH2:8]3.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:10]1[CH2:11][CH:12]2[CH:7]([CH2:6][C:5]3[S:1][CH:2]=[CH:3][C:4]=32)[CH2:8][CH2:9]1)=[O:22])[CH3:25]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
A 0° C. solution of product from Example 29, step h) (885 mg, 4.1 mmol) in CH2Cl2 (20 ml) was treated with triethylamine (1.71 ml, 12.3 mmol) and ethyl chloroformate (472 μl, 4.92 mmol) and the reaction was warmed to 22° C. Next, the reaction mixture was diluted with CH2Cl2 (20 ml) and washed with brine (25 ml). The organic layer was dried (MgSO4) and the solvent evaporated in vacuo to give the crude product that was purified by silica-gel chromatography (hexanes:EtOAc-50:50) to give 748 mg (73%) of the subtitle compound. MS calculated for C13H17NO2S+H 252, observed 252.
Workup
- washwashed with brine (25 ml)
- dry with materialThe organic layer was dried (MgSO4)
- customthe solvent evaporated in vacuo
- customto give the crude product that
- customwas purified by silica-gel chromatography (hexanes:EtOAc-50:50)
Sources & evidence
- ORD record
- ord-95593476d3f242ecb251377838df2120
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981919B2
Reaction notes
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