4-Fluorobenzonitrile → Methyl propionate

HRID 2373858Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:20][O:21][C:22](=[O:33])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH2:24].F[C:35]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=1>>[CH3:20][O:21][C:22](=[O:33])[CH2:23][CH3:25].[CH3:20][O:21][C:22](=[O:33])[C@@H:23]([NH:24][C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=2)=[CH:14][CH:13]=1)=[O:17])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)=[CH:30][CH:31]=1

Participants

Reactant 3

HCID 145174-Fluorobenzonitrile

HCID 70652Tyrosine Methyl Ester

HCID 27827194'-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

Product 2

HCID 11124Methyl propionate

HCID 11398657HCID 11398657, compound

Procedure

3-(4-Hydroxy-phenyl)-(2S)-[4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid methyl ester (664 mg) was prepared starting from 4′-trifluoromethyl-biphenyl-4-carboxylic acid (532 mg, 2.0 mmol) and tyrosine methyl ester (462 mg, 2.0 mmol) according to general procedure A. The above compound (443 mg, 1.0 mmol) was treated with 1-fluoro-4-cyanobenzene (181 mg, 1.5 mmol) following general procedure B to give 3-[4-(4-cyano-phenoxy)-phenyl]-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid methyl ester (360 mg). The ester was hydrolyzed following general procedure C to give the title compound (345 mg)

Sources & evidence

ORD record: ord-03f98717176545938a81758fa8c2a3cc
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459472B2

Reaction notes

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