Triphenylphosphine → HCID 67138199, compound

HRID 1592001Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].[CH2:20]([O:22][CH:23]([O:31][CH2:32][CH3:33])[C:24]1[S:28][C:27]([CH2:29]O)=[CH:26][CH:25]=1)[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:32]([O:31][CH:23]([O:22][CH2:20][CH3:21])[C:24]1[S:28][C:27]([CH2:29][N:8]2[S:7](=[O:13])(=[O:12])[N:6]([CH2:5][C:4]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:3]=3[O:2][CH3:1])[C:10](=[O:11])[CH2:9]2)=[CH:26][CH:25]=1)[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

The title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (13.9 g, 48.5 mmol), (5-diethoxymethyl-thiophen-2-yl)-methanol (10.5 g, 48.5 mmol) and triphenylphosphine (19.1 g, 72.2 mmol) are dissolved in dry THF (300 mL) and the mixture is cooled to 0° C. Diethyl azodicarboxylate (12. g, 72.7 mmol) is added dropwise over 3 min and the mixture is stirred at RT for 16 h. The solvent is evaporated and the residue is taken up in Et2O (100 mL). The solution is cooled to 0° C. and the precipitate is filtered and discarded. The filtrate is concentrated to dryness and the residue is chromatographed on silica gel using 0→100% EtOAc in hexane as the eluent to afford 5-(5-diethoxymethyl-thiophen-2-ylmethyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as an orange oil.

Workup

customThe solvent is evaporated
temperatureThe solution is cooled to 0° C.
filtrationthe precipitate is filtered
concentrationThe filtrate is concentrated to dryness
customthe residue is chromatographed on silica gel using 0→100% EtOAc in hexane as the eluent

Sources & evidence

ORD record: ord-353bb28b5c0441158566a22356fe8b7a
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291635B2

Reaction notes

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