Dichloromethane → HCID 68839077, compound

HRID 660695Notes

Reaction equation

[CH2:1]([CH:4]1[CH2:8][CH2:7][CH2:6][S:5]1(=[O:10])=[O:9])[C:2]#[CH:3].C(Cl)Cl.[CH2:14]([O:21][C:22]1[CH:27]=[C:26](I)[CH:25]=[CH:24][C:23]=1[N:29]1[S:33](=[O:35])(=[O:34])[N:32](CC[Si](C)(C)C)[C:31](=[O:42])[CH2:30]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].Cl[Cu].CCOC(C)=O>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([C:3]#[C:2][CH2:1][CH:4]2[CH2:8][CH2:7][CH2:6][S:5]2(=[O:10])=[O:9])[CH:25]=[CH:24][C:23]=1[N:29]1[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:42])[CH2:30]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-prop-2-ynyl-tetrahydrothiophene 1,1-dioxide (53 mg, 0.34 mmol) in 1 mL glyme/water (9:1) is added Pd(dppf)Cl2.CH2Cl2 (14 mg), a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (164 mg, 0.37 mmol) in 1 mL glyme/water (9:1), triethylamine (68 mg, 0.67 mmol) and CuCl (13 mg, 0.13 mmol). The mixture is heated at 120° C. in a microwave apparatus for 5 min then is poured into EtOAc. The mixture is washed with 1N HCl and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

washThe mixture is washed with 1N HCl
dry with materialthe organic phase is dried over magnesium sulfate
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-64f41d19b068442391676932b5cd8863
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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