[F:1][CH:2]([F:24])[CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5]C(=O)OCC1C=CC=CC=1.[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>[Pd].CO.C(Cl)Cl>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[NH2:5][CH2:4][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:2]([F:24])[F:1]A mixture of benzyl tert-butyl (3,3-difluoropropane-1,2-diyl)biscarbamate (195 g, 567 mmol) and palladium on carbon (10% w/w, 20 g) in methanol (2000 mL) was stirred at room temperature under a hydrogen atmosphere. After 16 hours, the reaction mixture was filtered and concentrated under reduced pressure. The residue was diluted with DCM (2500 mL) and oxalic acid (2.84 M solution in methanol, 200 mL, 567 mmol). After 2 hours, the mixture was filtered, and the collected solids were washed with DCM (500 mL) and dried in an oven under reduced pressure to afford tert-butyl (3-amino-1,1-difluoropropan-2-yl)carbamate oxalic acid salt. MS ESI calc'd. for C8H17F2N2O2 [M+H]+ 211. found 211. 1H NMR (400 MHz, D2O) δ 6.14-5.86 (m, 1H), 4.25 (d, J=12.8 Hz, 1H), 3.36 (d, J=14 Hz, 1H), 3.11-3.05 (m, 1H), 1.41 (s, 9H).
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