Triethylamine → (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester

HRID 852243Notes

Reaction equation

HRID 852243 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=C(Cl)OC(Cl)(Cl)Cl.[N-:25]=[C:26]=[O:27].Cl.[CH3:29][O:30][C:31](=[O:44])[C@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)N.C(N(CC)CC)C>O1CCOCC1.ClCCl>[CH3:29][O:30][C:31](=[O:44])[C@@H:32]([NH:25][C:26]([NH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])=[O:27])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 77956Benzenamine, 2-(phenylsulfonyl)-HCID 105034IsocyanateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 69377021(S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-benzenesulfonylphenylamine (1.88 g, 8.04 mmol) and diphosgene (0.48 ml, 4.02 mmol) in dioxane (25 ml) was heated at 60° C. for 16 h. The solvent was removed under reduced pressure. A solution of the crude isocyanate (8.04 mmol) in dichloromethane (14 ml) was slowly added to a solution of (S)-4-nitrophenylalanine methyl ester hydrochloride (2.31 g, 8.84 mmol) and triethylamine (3.7 ml, 26.52 mmol) in dichloromethane (14 ml) and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (100 ml) and washed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester (3.64 g, 94%) that was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting reaction mixture
  3. washwashed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab2ee6ba85184cce836201c6a9d369ea
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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