Tetrahydrofuran → HCID 178470115, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH2:17][CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-][CH:24]([CH3:26])[CH3:25])C.C1([C:30](C2CC2)=[S:31])CC1.[CH2:35]1[CH2:39]OC[CH2:36]1>>[CH:36]1([SH:31]([CH2:30][C:11]2([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][CH2:18][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:24]2[CH2:26][CH2:25]2)[CH2:35][CH2:39]1Participants
5
Procedure
To a stirred solution of ethyl N-(t-butoxycarbonyl)isonipecotate (1.06 g, 4.12 mmol) in THF (8 mL) at −78° C. was added LDA (1.5M, 2.75 mL, 4.12 mmol) dropwise, and the mixture was stirred for 30 minutes before addition of a solution of dicyclopropylthioketone (415 mg, 3.30 mmol) in THF (1 mL). After the addition, the reaction mixture was warmed to room temperature over 2 hours, quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford the title compound as a viscous oil (1.53 g, 96%), which was used in the next step without further purification.