Lithium Hydroxide → HCID 57433086, compound

To a solution of Ethyl (2S,3S,4S)-2-azido-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenylpentanoate (22 mg, 0.058 mmol) in 50% MeOH/THF (800 μL) was added aqueous 1N LiOH (70 μL, 0.070 mmol). The reaction was stirred at rt overnight and concentrated in vacuo. The resulting residue was suspended in EtOAc (30 mL) and washed with aqueous 10% KHSO4 solution (15 ml) and brine (15 mL), and the organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel using an isocratic elution of 10% (10% AcOH/MeOH)/CH2Cl2 and collection and concentration of the appropriate fractions yielded the compound as a yellow residue. 1H NMR (400 MHz, CD3OD) δ 7.23 -7.15 (m, 5H), 4.23-3.87 (m, 3H), 3.21-3.08 (m, 1H), 2.66-2.57 (m, 1H), 1.29 (s, 9H); ES MS (M+23)=373.

1. concentrationconcentrated in vacuo
2. washwashed with aqueous 10% KHSO4 solution (15 ml) and brine (15 mL)
3. extractionthe organic extract
4. dry with materialwas dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification of the residue by flash column chromatography on silica gel using
8. washan isocratic elution of 10% (10% AcOH/MeOH)/
9. customCH2Cl2 and collection and concentration of the appropriate fractions
10. customyielded the compound as a yellow residue

ORD record

ord-3ca17de33d8d4ea5ad3429c216f70345

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003653B2