Hydrochloric Acid → Methyl (2S)-2-amino-3-(4-bromophenyl)propanoate

反応式

[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1.Cl.[CH3:15]O>>[NH2:1][C@H:2]([C:11]([O:13][CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[CH:8][CH:9]=1

参加物

反応物 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 6712144-Bromo-L-phenylalanine

生成物 1

HCID 24720903Methyl (2S)-2-amino-3-(4-bromophenyl)propanoate

実験手順

1.0 g (4.01 mmol) H-Phe(4-Br)—OH were refluxed in 20 ml methanol with 2.1 ml HCl (4 M in 1,4-dioxane) over night. Evaporation of the solvent gave H-Phe(4-Br)—OMe*HCl as white solid. 1.0 g (3.4 mmol) of this hydrochloride and 1.7 ml (10.2 mmol) DIPEA were suspended in 8 ml THF and 0.41 ml (3.4 mmol) 2,4,6-trimethylbenzoyl chloride were added dropwise at 0° C. After 18 h at room temperature the reaction was quenched with water and the solvent was removed. The residue was suspended in ethyl acetate, washed with saturated Na2SO4 and brine to give compound (13) as an oil.

後処理

customEvaporation of the solvent

出典と根拠

ORDレコード: ord-89c55b79e431430383c54221e7ef7434
出典データセット: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08927534B2

反応ノート

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