2,2-Difluoroethyl trifluoromethanesulfonate → HCID 86729795, compound

HRID 1027591Notes

Reaction equation

HRID 1027591 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][O:11][NH:10][C:9]1=[O:13])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O[CH2:21][CH:22]([F:24])[F:23])(=O)=O>>[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]1[CH2:12][O:11][N:10]([CH2:21][CH:22]([F:24])[F:23])[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 5225473HCID 5225473, compound

Product 1

HCID 86729795HCID 86729795, compoundYield 34.9%

Procedure

As described in Example 4, Step A, (3-oxo-isoxazolidin-4-yl)-carbamic acid tert-butyl ester (0.30 g) was alkylated with 2,2-difluoroethyl trifluoromethanesulfonate (0.35 g). to afford the title product as a white solid (138 mg); 1H-NMR (CDCl3, 400 MHz): 6.05 (tt, 1H), 5.10 (m, 1H), 4.90 (m, 1H), 4.35 (dt, 2H), 4.20 (dd, 1H), 1.50 (s, 9H); along with the O-alkylated product (179 mg): 1H-NMR (CDCl3, 400 MHz): 5.95 (tt, 1H), 4.80 (m, 1H), 4.60 (m, 1H), 3.80-4.10 (m, 3H), 1.50 (s, 9H).

Sources & evidence

ORD record
ord-b721639c36774416a04be699193515c3
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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