4-Fluorobenzenesulfonyl chloride → (S)-3-(4-benzyloxy-phenyl)-2-(4-fluoro-benzenesulfonylamino)-propionic acid

HRID 378934Notes

Reaction equation

HRID 378934 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@H:2]([NH:1][S:28]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 725701O-benzyl-L-tyrosine

Product 1

HCID 54304605(S)-3-(4-benzyloxy-phenyl)-2-(4-fluoro-benzenesulfonylamino)-propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid (2.7 g, 0.010 mol), 4-fluoro-benzenesulfonyl chloride (2.0 g, 0.010 mol), and sodium carbonate (2.2 g, 0.020 mol) in a mixture of tetrahydrofuran (20 mL) and water (20 mL) was stirred at room temperature for 3 days. The reaction mixture was partitioned between ethyl acetate and 1 M hydrochloric acid. The organic layer was washed with saturated sodium chloride solution, dried (MgSO4), and rotary-evaporated under reduced pressure to give an oil. The oil was chromatographed on silica gel (445 g, 230-400 mesh) eluting with dichloromethane-methanol (20:1), and the fractions containing product were rotary-evaporated to give a solid. The solid was recrystallized from toluene to give the title compound as a light yellow solid; yield 0.22 g (5%), mp=138-139° C.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1 M hydrochloric acid
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customrotary-evaporated under reduced pressure
  5. customto give an oil
  6. customThe oil was chromatographed on silica gel (445 g, 230-400 mesh)
  7. washeluting with dichloromethane-methanol (20:1)
  8. additionthe fractions containing product
  9. customwere rotary-evaporated
  10. customto give a solid
  11. customThe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-862f5416262247f388c7f3af6f65d114
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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