Water → HCID 68295198, compound

HRID 1184946Notes

Reaction equation

HRID 1184946 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:10]([NH:12][C@H:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH2:14][C:15]([OH:17])=[O:16])=[O:11])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].O>CN(C=O)C.C1(B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C@@H:13]([NH:12][C:10]([C:4]1[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1)=[O:11])[CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 2

HCID 962WaterHCID 68294625HCID 68294625, compound

Product 1

HCID 68295198HCID 68295198, compoundYield 59.9%

Reagents, catalysts & solvents 3

HCID 10340Sodium CarbonateCatalystHCID 66827Phenylboronic AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 50 mg (0.13 mmol) of (S)-3-[(5-Chloro-6-methoxy-pyridine-3-carbonyl)-amino]-3-(2-chloro-phenyl)-propionic acid in 3 ml of DMF are added: 25 mg (0.21 mmol, 1.5 eq) phenylboronic acid, 60 mg Na2CO3 (0.56 mmol, 4.2 eq) and 10 mg (0.13 eq) DI-MICRO-CHLOROBIS[2-[(DIMETHYLAMINO)METHYL]PHENYL-C,N]DIPAL as catalyst. After the addition of 1 ml of water the resulting mixture is heated to 100° C. for 6 hours, the reaction is filtered via a pad of celite and the resulting solution subjected to preparative HPLC chromatography yielding 16 mg of product (Yield: 29%).

Workup

  1. filtrationthe reaction is filtered via a pad of celite

Sources & evidence

ORD record
ord-7a80fbb882c240dd9827e922cfdf6df1
Source dataset
uspto-grants-2014_03
Patent number
US08669370B2

Reaction notes

Loading…