Water → (S)-3-(4-Hydroxy-phenyl)-2-[4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

HRID 1601117Notes

Reaction equation

HRID 1601117 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][CH:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.O>C1(SC)C=CC=CC=1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:31][CH2:32][CH:33]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:34][CH2:35]3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12114675(S)-3-(4-Benzyloxy-phenyl)-2-[4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

Product 1

HCID 54127504(S)-3-(4-Hydroxy-phenyl)-2-[4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid

Reagents, catalysts & solvents 1

HCID 7520ThioanisoleSolvent

Procedure

To a room temperature, stirred mixture of (S)-3-(4-benzyloxy-phenyl)-2-[4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-propionic acid (0.033 g, 0.000058 mol) in thioanisole (0.34 mL) was added trifluoroacetic acid (1 mL), and the mixture was stirred for 18 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and rotary-evaporated under reduced pressure to remove volatiles. The resulting yellow solution was chromatographed on silica gel (5.5 g) eluting with dichloromethane (10×5 mL) followed by dichloromethane-methanol (14:1). Fractions containing product were rotary-evaporated. The residue was suspended in water and stirred to give the title compound as an off-white solid; yield 0.0079 g (28%), mp=108-110° C.

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customrotary-evaporated under reduced pressure
  5. customto remove volatiles
  6. customThe resulting yellow solution was chromatographed on silica gel (5.5 g)
  7. washeluting with dichloromethane (10×5 mL)
  8. additionFractions containing product
  9. customwere rotary-evaporated
  10. stirringstirred

Sources & evidence

ORD record
ord-90496a96979742d0a9312b088e431b81
Source dataset
uspto-grants-1999_11
Patent number
US05977141

Reaction notes

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