3-Bromo-5-fluoroanisole → L-m-tyrosine

HRID 1529836Notes

Reaction equation

HRID 1529836 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:10](F)[CH:9]=1)[C:3]([O:5]C)=[O:4].BrC1C=C(OC)C=C(F)C=1.NC(CC1C=C(O)C=C(F)C=1)C(OC)=O>>[CH:10]1[CH:11]=[C:12]([OH:14])[CH:13]=[C:8]([CH2:7][C@H:2]([NH2:1])[C:3]([OH:5])=[O:4])[CH:9]=1

Participants

4

Reactant 3

HCID 108220943-Bromo-5-fluoroanisoleHCID 67981259Methyl 2-amino-3-(3-fluoro-5-hydroxyphenyl)propanoateHCID 68379885(S)-methyl 2-amino-3-(3-fluoro-5-hydroxyphenyl)propanoate

Product 1

HCID 6950578L-m-tyrosine

Procedure

(S)-methyl 2-amino-3-(3-fluoro-5-hydroxyphenyl)propanoate was purchased from NetChem (USA). (3-bromo-5-fluoroanisole (9-1) was purchased from Accela ChemBio Co., Ltd., (Shanghai, China) and can also be purchased from Amfinecom Inc (USA) or Apollo Scientific Ltd. (UK)). DL-5-fluoro-meta-tyrosine (9) and methyl 2-amino-3-(3-fluoro-5-hydroxyphenyl)propanoate (10)) were synthesised as follows.

Sources & evidence

ORD record
ord-1f72db6e45164810b31dcb6b2d6fce6a
Source dataset
uspto-grants-2015_07
Patent number
US09090657B2

Reaction notes

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