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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2373794Generated: October 30, 2026

Methylamine → 3'-Chloro-4'-fluoro-4-hydroxy-biphenyl-3-carboxylic acid (2-biphenyl-4-yl-1(S)-methylcarbamoyl-ethyl)-amide

https://huagongshe.com/reaction/2373794

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
ReactantTetrahydrofuranHCID 8028—
Reactant3-(Biphenyl-4-yl)-(2S)-[(3'-chloro-4'-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic Acid Methyl EsterHCID 11386560—
Reactant3-(Biphenyl-4-yl)-(2S)-[(3'-chloro-4'-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic acidHCID 58717651—
ReactantTMSBr TFA DCMHCID 86597135—
Product3'-Chloro-4'-fluoro-4-hydroxy-biphenyl-3-carboxylic acid (2-biphenyl-4-yl-1(S)-methylcarbamoyl-ethyl)-amideHCID 59852595—

Reaction Steps

Resin bound 3-(Biphenyl-4-yl)-(2S)-[(3′-chloro-4′-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic acid (30 mg, 0.09 mmol) prepared from resin bound 3-(Biphenyl-4-yl)-(2S)-[(3′-chloro-4′-fluoro-4-hydroxy-biphenyl3-carbonyl)-amino]-propionic acid methyl ester following general procedure C, was reacted with methyl amine in THF(0.45 mmol) as described in general procedure A, then cleaved with TMSBr/TFA/DCM (1:1:5) at rt for 4 h. The residue obtained after removing the solvent was purified by chromatography to give the title compound. (36 mg). LC/MS (m/z): 503 (M+1)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07459472B2
Source datasetuspto-grants-2008_12
ORD IDord-ad4486667faf474c95cc4dafd31bef55
Source noteuspto-grants-2008_12