HCID 86590986, compound → HCID 86590988, compound

A suspension of 5% Pd—C (0.175 g) in EtOAc (10 mL) was stirred for 1.5 hours under H2 atmosphere and a solution of the azido alcohol 12 (0.373 g, 1.621 mmol) in EtOAc (15 ml) was added portionwise. The reaction mixture was stirred for 17 hours under H2 and was evaporated to dryness. The residue was washed with dry ether (3×15 mL) and the product was extracted from the dried residue with hot (ca. 70° C.) water (30 mL). The aqueous solution was filtered through a paper filter and the black solid was washed with hot water (3×10 mL). Evaporation of the filtrate in vacuo provided 0.296 g (90%) of the product 13 as a white solid with mp 200-202° C. (decomp.). 1H NMR (400 MHz) in CD3OD+1 drop of CF3CO2H (J, Hz): δ 1.52 (3H, d, 3J=7.4, α-MeCH), 4.08 (1H, dd, 2J=−11.7, 3J=2.5, 6-HA), 4.18-4.16 (2H, m, 4-H, 5-H), 4.46-4.41 (1H, dd, 2J=−11.7, 3J=6.4, 6-HB), 4.98 (1H, q, 3J=7.4, α-CH). 13C (100 MHz) in D2O: δ 17.62, 59.62, 61.42, 73.69, 82.48, 169.06, 180.86. IR (KBr), cm−1: 3158, 1684, 1599, 1568, 1400. MS (CI, isobutane), m/Z: 205 (M++1). Anal. Calcd for C7H12N2O5+0.5 H2O: C, 39.4; H, 6.1; N, 13.1. Found: C, 39.3; H, 6.2; N, 13.2%.

1. stirringThe reaction mixture was stirred for 17 hours under H2
2. customwas evaporated to dryness
3. washThe residue was washed with dry ether (3×15 mL)
4. extractionthe product was extracted from the dried residue with hot (ca. 70° C.) water (30 mL)
5. filtrationThe aqueous solution was filtered through a paper
6. filtrationfilter
7. washthe black solid was washed with hot water (3×10 mL)
8. customEvaporation of the filtrate in vacuo

ORD record

ord-a92214de1b7d4828b7a98c83ab08c8b7

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06861416B2