1,2-Dichloroethane → 2-(benzyloxy)-2-oxoethyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate

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Reaction Steps

4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)-benzoic acid (see for reference procedure Example 18, WO 2010/089107, which is incorporated herein by reference in its entirety) (2.5 g, 6.49 mmol), benzyl 2-hydroxyacetate (1.078 g, 6.49 mmol), EDC (3.73 g, 19.46 mmol) and DMAP (0.396 g, 3.24 mmol) were mixed in DCM (150 ml), and the resulting mixture was stirred at RT for 24 hours. Then the mixture was washed with HCl 1N and NaHCO3 sat. sol.; the organic layer was dried over Na2SO4, and the solvent was evaporated. The crude was sonicated in MeOH; 2-(benzyloxy)-2-oxoethyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate precipitated (2.6 g, 4.87 mmol, 75% yield, MS/ESI+ 556.0 [MNa]+), it was filtered and used as such in the following reaction without further purification.

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