O-benzyl-L-serine → Propanoic acid, 2-bromo-3-(phenylmethoxy)-, (S)-

HRID 464566

Reaction equation

[C:1]1([CH2:7][O:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:15].[Na+].N([O-])=O.[Na+]>S(=O)(=O)(O)O>[Br:15][C@@H:10]([CH2:9][O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of O-(phenylmethyl)-L-serine (21.6 g, 0.108 mol) in aqueous sulfuric acid (786 ml, 2.5N) containing sodium bromide (69.3 g, 6.0 eq) was cooled to 0° C. in an ice bath. Sodium nitrite (21 g, 2.7 eq) was added over 10 minutes, and the solution stirred at 0° C. for one hour. The cooling bath was removed, ether (250 ml) was added, and stirring was continued overnight at room temperature. The aqueous layer was extracted repetitively with ether (3×100 ml), and the combined extracts were dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give 25 g of a crude product. The product was purified by column chromatography (83:17; petroleum ether:ethyl acetate) to yield the title compound (10.6 g).

Workup

customThe cooling bath was removed
additionether (250 ml) was added
stirringstirring
waitwas continued overnight at room temperature
extractionThe aqueous layer was extracted repetitively with ether (3×100 ml)
dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customto give 25 g of a crude product
customThe product was purified by column chromatography (83:17; petroleum ether:ethyl acetate)

Sources & evidence

ORD record: ord-378505d06e3c4158a224f14682c12fae
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04548751

Linked notes

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