Triethylamine → (2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

HRID 2122023Notes

Reaction equation

HRID 2122023 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:5]([S:12][CH2:13][CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.COC(=O)[C@H](N)[C@H](SCC)C1C=CC=CC=1.C(N(CC)CC)C.FC1C=CC(C2C=CC(S(Cl)(=O)=O)=CC=2)=CC=1>C(Cl)Cl>[CH2:13]([S:12][C@H:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C@@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:3]([OH:32])=[O:2])[CH3:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27947494'-Fluorobiphenyl-4-sulfonyl chlorideHCID 69881323(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl esterHCID 69882615(2S,3R)-2-amino-3-ethylsulfanyl-3-phenyl-propionic acid methyl ester

Product 1

HCID 9825456(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2S,3R)-3-Ethylsulfanyl-2-(4′-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl ester. To a solution of (2S,3R)-2-amino-3-ethylsulfanyl-3-phenyl-propionic acid methyl ester 4a (49 mg, 0.20 mmol) in methylene chloride (2.0 mL) is added triethylamine (0.060 mL, 0.43 mmol) and 4′-fluoro-4-biphenylsulfonyl chloride (66 mg, 0.24 mmol). This mixture is stirred under argon overnight at room temperature. The reaction is diluted with methylene chloride and washed with 1.0 N aq. HCl. The aqueous layer is extracted with methylene chloride. The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes) to give the desired product.

Workup

  1. washwashed with 1.0 N aq. HCl
  2. extractionThe aqueous layer is extracted with methylene chloride
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-26b264d9ff03404fbef14fb6ef965191
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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