Water → HCID 86052307, compound

HRID 1782038Notes

Reaction equation

HRID 1782038 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[Cl:18][C:19]1[CH:30]=[C:29]([Cl:31])[C:28]([OH:32])=[CH:27][C:20]=1[O:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:26][O:25][C:23](=[O:24])[CH2:22][O:21][C:20]1[CH:27]=[C:28]([O:32][CH2:4][CH:2]2[CH2:3][O:1]2)[C:29]([Cl:31])=[CH:30][C:19]=1[Cl:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 86052306HCID 86052306, compound

Product 1

HCID 86052307HCID 86052307, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (0.4 g), methyl (2,4-dichloro-5-hydroxyphenoxy)acetate (0.39 g) and Cs2CO3 (0.58 g) in DMF (2 ml) was stirred at r.t. overnight. Water was added and (2,4-dichloro-5-oxiranylmethoxy-phenoxy)-acetic acid methyl ester (0.22 g) was isolated by filtration and dried in vacuo. 5-Chloro-3H-spiro[1-benzofuran-2,4′-piperidine] (0.16 g) in ethanol (5 ml) was added and heated at 70° C. for 2 h. The mixture was allowed to cool and water (1 ml) followed by LiOH (2 eq) was added. Stirred for 3 h. RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.): acetonitrile) gave the title compound (0.1 g) as a white solid.

Sources & evidence

ORD record
ord-177ff963ef76464a9e574524c23659ed
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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