Pyridine → 3-Biphenyl-4-yl-2-[5-bromo-2-(4-tert-butyl-benzenesulfonylamino)-benzoylamino]-propionic acid methyl ester

HRID 1784229Notes

Reaction equation

HRID 1784229 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[NH2:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.N1C=CC=CC=1.[C:36]([C:40]1[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=1[NH:27][S:46]([C:43]1[CH:44]=[CH:45][C:40]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:41][CH:42]=1)(=[O:48])=[O:47])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 68860272(2S)-(2-amino-5-bromo-benzoyl-amino)-3-biphenyl-4-yl-propionic acid methyl ester

Product 1

HCID 219212433-Biphenyl-4-yl-2-[5-bromo-2-(4-tert-butyl-benzenesulfonylamino)-benzoylamino]-propionic acid methyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (2S)-(2-amino-5-bromo-benzoyl-amino)-3-biphenyl-4-yl-propionic acid methyl ester (1.0 g, 2 mmol) prepared above dissolved in DCM containing pyridine (1.58 g, 4 mmol), was added 4-tert-butylbenzenesulfonyl chloride (1.20 g, 2.5 mmol) at 0° C. The reaction mixture was stirred at rt for 3 h, extracted with DCM, washed with 1M HCl and brine, and was concentrated in vacuo, followed by column chromatography purification (silica, CH2Cl2) giving 3-biphenyl-4-yl-2-[5-bromo-2-(4-tert-butyl-benzenesulfonylamino)-benzoylamino]-propionic acid methyl ester (1.25 g) as a white solid which was hydrolyzed according to Procedure C yielding the title compound (1.23 g) as a white solid.

Workup

  1. extractionextracted with DCM
  2. washwashed with 1M HCl and brine
  3. concentrationwas concentrated in vacuo
  4. customfollowed by column chromatography purification (silica, CH2Cl2)

Sources & evidence

ORD record
ord-ab00b5f3e45e4be3a73101d5ff61a76e
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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