Anisole → N-(4'-Bromo[1,1'-biphenyl]-4-sulfonyl)-L-valine

HRID 1292245Notes

Reaction equation

HRID 1292245 reaction equation
C1(OC)C=CC=CC=1.C([O:13][C:14](=[O:36])[C@@H:15]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17])(C)(C)C>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[Br:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[CH:25]=[CH:24][C:23]([S:20]([NH:19][C@@H:15]([CH:16]([CH3:18])[CH3:17])[C:14]([OH:36])=[O:13])(=[O:22])=[O:21])=[CH:28][CH:27]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 10695590HCID 10695590, compound

Product 1

HCID 9887870N-(4'-Bromo[1,1'-biphenyl]-4-sulfonyl)-L-valineYield 96%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of anisole (4.9 g, 0.045 mol) in trifluoroacetic acid (200 mL) was added in small portions the tert-butyl ester (21.1 g) prepared in Step (c). The solution was stirred at room temperature for 16 hours, then poured over ice. The aqueous suspension was diluted with chloroform, the layers separated, and the organic portion was washed with saturated sodium chloride, dried (MgSO4) and concentrated to dryness. The resulting solid was suspended in hexanes/diethyl ether (9:1) and collected by filtration to give the title compound (17.7 g, 96%) as a white solid, mp 192°-193° C.

Workup

  1. additionpoured over ice
  2. customthe layers separated
  3. washthe organic portion was washed with saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-690e4540a57345aaa64e42c9aaf041a2
Source dataset
uspto-grants-1998_05
Patent number
US05756545

Reaction notes

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