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

HRID 1784244Notes

Reaction equation

HRID 1784244 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[O:35]([C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:45]2[CH:46]=[CH:47][C:42]([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:43][CH:44]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 68860011(S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 68858977(S)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-3-(4'-phenoxy-biphenyl-4-yl)-propionic acid methyl esterYield 33.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (273 mg, 0.53 mmol), Pd (PPh3)4 (96 mg, 0.11 mmol), and 4-phenoxyphenylboronic acid (226 mg, 1.1 mmol) were dissolved in 5 mL of toluene, a 1M Na2CO3 solution (1.3 mL, 1.3 mmol) added and the mixture heated at 80° C. for 16 h. The reaction mixture was evaporated to dryness and the crude mixture purified over silica gel (8:2, DCM-hexanes) to give (S)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-3-(4′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester (107 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe crude mixture purified over silica gel (8:2, DCM-hexanes)

Sources & evidence

ORD record
ord-ec6e09a7ec42436d89a4275b9ece9d8d
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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