Sodium Carbonate → (2S)-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-3-(4'-phenoxy-biphenyl-4-yl)-propionic acid

HRID 1784239Notes

Reaction equation

HRID 1784239 reaction equation
C[O:2][C:3](=[O:35])[C@@H:4]([NH:13][C:14](=[O:34])[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[NH:22][CH2:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[O:36]([C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([NH:22][CH2:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][CH:25]=2)=[C:15]([CH:20]=1)[C:14]([NH:13][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:46]2[CH:47]=[CH:48][C:43]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:44][CH:45]=2)=[CH:10][CH:11]=1)[C:3]([OH:2])=[O:35])=[O:34]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 68862809(S)-3-(4-Bromo-phenyl)-2-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 58717951(2S)-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-3-(4'-phenoxy-biphenyl-4-yl)-propionic acidYield 52.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-3-(4-Bromo-phenyl)-2-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (150 mg, 0.36 mmol), Pd (PPh3)4 (84 mg, 0.072 mmol), and 4-phenoxyphenylboronic acid (233 mg, 1.09 mmol) were dissolved in 5 mL of toluene, a 1M Na2CO3 solution (0.9 mL, 0.91 mmol) added and the mixture heated at 80° C. for 12 h. The reaction mixture was diluted with 5 mL of CH2Cl2 and filtered, all volatiles are removed under vaccum and the ester product was hydrolyzed according to Procedure C, and purified over silica gel (ethyl acetate:hexanes) to give the title compound(118 mg) as a white solid.

Workup

  1. filtrationfiltered
  2. customall volatiles are removed under vaccum
  3. custompurified over silica gel (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-99513236d4c84c22b8b4e88da40b7cd7
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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