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

HRID 1424317노트

반응식

[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

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 6712144-Bromo-L-phenylalanine

생성물 1

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

실험 절차

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.

후처리

customEvaporation of the solvent

출처 및 근거

ORD 기록: ord-89c55b79e431430383c54221e7ef7434
출처 데이터셋: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08927534B2

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