Trifluoroacetic acid → 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

HRID 1884278Notes

Reaction equation

HRID 1884278 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]=[CH2:18])[C:12]([O:14]C)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C[O:26]C(=O)CN(CC=C)C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.C(N(CC)CC)C.[C:55]1(C2C=CC=CC=2)[CH:60]=[CH:59][C:58]([S:61](Cl)(=O)=O)=[CH:57][CH:56]=1>C(Cl)Cl.O>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]([OH:26])[CH2:18][S:61][C:58]2[CH:59]=[CH:60][CH:55]=[CH:56][CH:57]=2)[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 22243128N-Boc-allylglycine methyl esterHCID 23508264Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate

Product 1

HCID 235082932-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate: To a solution of N-Boc-allylglycine methyl ester 1a (4.0 g, 17.6 mmol) in CH2Cl2 (15 mL) is added trifluoroacetic acid (10 mL) slowly, and the resulting mixture is stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure to dryness then dissolved in dioxane (15 mL) and water (15 mL). To the solution is added triethyl amine (9.8 mL, 70.4 mmol), followed by biphenyl-4-sulfonyl chloride (5.9 g, 21.12 mmol) and the mixture is stirred overnight. The reaction mixture is diluted with water, extracted three times with EtOAc. The combined EtOAc layer is washed with 1 N HCl, H2O, brine, dried, and concentrated to an oil which solidified upon standing. The crude product is recrystallized from EtOAc/hexane to give the desired product.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure to dryness
  2. dissolutionthen dissolved in dioxane (15 mL)
  3. stirringthe mixture is stirred overnight
  4. extractionextracted three times with EtOAc
  5. washThe combined EtOAc layer is washed with 1 N HCl, H2O, brine
  6. customdried
  7. concentrationconcentrated to an oil which
  8. customThe crude product is recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-cae399ce3dd94f85b68234d4e4f09ade
Source dataset
uspto-grants-2004_07
Patent number
US06762198B2

Reaction notes

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