Sodium Carbonate → HCID 69205065, compound

HRID 2373834Notes

Reaction equation

HRID 2373834 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@@H:4]([NH:13][C:14]([C:16]1[CH:17]=[C:18]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[F:36][C:37]([F:48])([F:47])[C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][CH:43]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:35])[C@@H:4]([NH:13][C:14]([C:16]1[CH:17]=[C:18]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:42]2[CH:41]=[CH:40][CH:39]=[C:38]([C:37]([F:48])([F:47])[F:36])[CH:43]=2)=[CH:8][CH:7]=1.[CH2:23]([O:22][C:21]1[CH:20]=[CH:19][C:18]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)=[CH:17][C:16]=1[C:14]([NH:13][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:42]2[CH:41]=[CH:40][CH:39]=[C:38]([C:37]([F:48])([F:47])[F:36])[CH:43]=2)=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:35])=[O:15])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 69205054HCID 69205054, compound

Product 2

HCID 69205065HCID 69205065, compoundHCID 69207989HCID 69207989, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
76 °C

Procedure

2-(S)-[(4-Butoxy-3′-chloro-4′-fluoro-biphenyl-3-carbonyl)-amino]-3-(3′-trifluoromethyl-biphenyl-4-yl)-propionic acid methyl ester was prepared following General Procedure D using 3-(4-bromo-phenyl)-2-(S)-[(4-Butoxy-3′-chloro-4′-fluoro-biphenyl-3-carbonyl)-amino]-propionic acid methyl ester ((0.677 g, 1.19 mmol), 3-trifluoromethyl-benzene boronic acid (0.349 g, 1.8 mmol), palladium tetrakis-triphenylphosphine (69 mg, 0.06 mmol), and Na2CO3(aq) (2.0 N, 5 mL, 10 mmol) in DME (10 mL). The mixture was heated at 76° C. for 19 h. Purification by flash chromatography (ethyl acetate/hexanes 1:5, 1:4) gave the methyl ester of the title compound (177 mg, 0.28 mmol).

Workup

  1. customPurification by flash chromatography (ethyl acetate/hexanes 1:5, 1:4)

Sources & evidence

ORD record
ord-b96a88cb288b4b1789f0e0eed328906f
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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