Sodium Carbonate → HCID 58717891, compound

HRID 1984803Notes

Reaction equation

HRID 1984803 reaction equation
C[O:2][C:3](=[O:31])[C@@H:4]([NH:13][C:14](=[O:30])[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[F:32][C:33](B(O)O)([F:35])[F:34].[C:39]([O-:42])([O-])=O.[Na+].[Na+]>[Pd]>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:15]([CH:20]=1)[C:14]([NH:13][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:5]2[CH:6]=[CH:7][C:39]([O:42][C:33]([F:35])([F:34])[F:32])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1)[C:3]([OH:2])=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21921459(Trifluoromethyl)boronic acidHCID 68868394HCID 68868394, compound

Product 1

HCID 58717891HCID 58717891, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was then prepared from 3-(4-bromo-phenyl)-(2S)-(5-chloro-2-heptyloxy-benzoylamino)-propionic acid methyl ester (0.090 g, 0.176 mmol) and trifluoromethyl boronic acid (0.067 g, 0.352 mmol) with Pd (PPh3) (0.020 g, 0.0176 mmol) and 2 N Na2CO3 (0.528 ml, 0.528 mmol) as per general procedure D to yield the (2S)-(5-chloro-2-heptyloxy-benzoylamino)-3-(4′-trifluoromethoxy-biphenyl-4-yl)-propionic acid methyl ester which was further hydrolyzed as per general procedure C to give the title compound (0.050 g).

Sources & evidence

ORD record
ord-d1f08ce1ae0444c3a1a8629175449d18
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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