Sodium Carbonate → (2S)-(2-Amino-5-chloro-benzoylamino)-3-(4'-cyclohexyl-biphenyl-4-yl)propionic acid methyl ester

HRID 1245108Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[NH2:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[CH:25]1([C:31]2[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:13][C:14](=[O:23])[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[NH2:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:28]2[CH:27]=[CH:26][C:25]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:30][CH:29]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(2S)-(2-Amino-5-chloro-benzoylamino)-3-(4′-cyclohexyl-biphenyl-4-yl)propionic acid methyl ester compound was prepared following General Procedure D using (S)-2-(2-amino-5-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (1.803 g, 4.38 mmol), 4-cyclohexyl-benzene boronic acid (1.61 g, 98%, 7.88 mmol), palladium tetrakis-triphenylphosphine (0.462 g, 0.4 mmol), and aqueous Na2CO3 (2.0 N, 16 mL, 32 mmol) in DME (32 mL). The mixture was heated at 80° C. for 14 h. Purification by flash chromatography (ethyl acetate/hexanes 1:3, 1:2) gave product as a red solid (2.01 g, 4.09 mmol, 93% yield).

Workup

customPurification by flash chromatography (ethyl acetate/hexanes 1:3, 1:2)

Sources & evidence

ORD record: ord-b05ff1ad822e428da7ce07c969b37e4d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122580B2

Reaction notes

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