Sodium Nitrite → HCID 57262022, compound

Temperature

-9 °C

To a stirred suspension of crude amino acid salt (2S,3S)-2-amino-3-(methoxycarbonyl)pentanoic acid hydrobromide (19.6 g) of Example 7 in aqueous hydrobromic acid (2.5N), cooled to -9° C. with an ice water-salt-acetone bath, was added sodium nitrite (10.0 g, 144.9 mmol) in small portions over a 1.5 h period, keeping the internal temperature (measured by electronic internal temperature probe) below -7° C. The reaction mixture was stirred for 2 h in the cooling bath after the addition was complete, then it was extracted with ethyl acetate (2×500 mL). The combined organic layers were washed with saturated aqueous sodium chloride (2×250 mL), dried (MgSO4), and concentrated in vacuo to give the bromoacid which slowly solidified to a waxy solid (13.0 g).

1. customthe internal temperature (measured by electronic internal temperature probe) below -7° C
2. additionafter the addition
3. extractionit was extracted with ethyl acetate (2×500 mL)
4. washThe combined organic layers were washed with saturated aqueous sodium chloride (2×250 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto give the bromoacid which

ORD record

ord-1547a1983e9c48269eb0b46f13c24bc4

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05322942