Boc-4-amino-3-hydroxybutanoic acid → HCID 71565328, compound

Temperature

0 °C

To a borane tetrahydrofuran complex solution 1M in tetrahydrofuran (15 ml) was added at 0° C. under an atmosphere of argon a solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (1.5 g) in tetrahydrofuran (35 ml). The reaction mixture was stirred at 0° C. for 3 hours. The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml). Ethyl acetate was added (250 ml) and the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified over silica gel (ethyl acetate/methanol 9:1) to give (2,4-dihydroxy-butyl)-carbamic acid tert-butyl ester (0.83 g).

1. customThe reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml)
2. additionEthyl acetate was added (250 ml)
3. washthe mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml)
4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
5. concentrationconcentrated
6. customThe residue was purified over silica gel (ethyl acetate/methanol 9:1)

ORD record

ord-e93c1fbbbf574253a561f731a5cfb4b6

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09307766B2