Sulfuric Acid → HCID 21197492, compound

HRID 2174322Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:18].[Na+].N([O-])=O.[Na+].S(=O)(=O)(O)O>Br.C(OCC)C>[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:18])[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of L-glutamic acid-5-benzylester (Fluka, 3.0 g, 0.013 mol) and sodium bromide (Fisher, 4.6 g, 0.044 mol) in aqueous hydrobromic acid (Fluka, 1 M, 22.5 mL) cooled to 0° C. was added portion wise sodium nitrite (Fluka, 1.6 g, 0.023 mol). After stirring for 2 h at 0° C., concentrated sulphuric acid (Merck, 1.2 mL) was added followed by diethyl ether (Eternell). The water phase was extracted three times with diethyl ether. The combined organic phases was washed four times with brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified using normal phase chromatography (Silica column (40 g), solvents: A=hexane, B=ethyl acetate, gradient: 10-35% B over 20 min, flow rate 40 mL/min, UV detection at 214 and 254 nm) affording 1.81 g of the pure product. Yield 46%. Structure verified by NMR.

Workup

extractionThe water phase was extracted three times with diethyl ether
washThe combined organic phases was washed four times with brine
dry with materialdried over sodium sulphate
customevaporated under reduced pressure
customThe crude product was purified
waitA=hexane, B=ethyl acetate, gradient: 10-35% B over 20 min

Sources & evidence

ORD record: ord-ae2e8815d8234846b256a58befcde04c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061080B2

Reaction notes

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