Triethylamine → (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-hydroxyphenyl) propionic acid methyl ester
Reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]=[C:17]=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:20][O:21][C:22](=[O:33])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH2:24].C(N(CC)CC)C>ClCCl>[CH3:20][O:21][C:22](=[O:33])[C@@H:23]([NH:24][C:17]([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:8])=[O:9])=[O:18])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-benzenesulfonylphenyl isocyanate (600 mg, 2.31 mmol, prepared as described in Preparation 20) in dichloromethane (4 ml) was slowly added to a solution of L-tyrosine methyl ester hydrochloride (589 mg, 2.54 mmol) and triethylamine (0.64 ml, 4.62 mmol) in dichloromethane (4 ml) and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (50 ml) and washed with hydrochloric acid 1N (2×20 ml), saturated aqueous NaHCO3 (2×20 ml) and brine (1×20 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield the title compound (930 mg, 89%) as a viscous oil.
Workup
- customthe resulting reaction mixture
- washwashed with hydrochloric acid 1N (2×20 ml), saturated aqueous NaHCO3 (2×20 ml) and brine (1×20 ml)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d0ffd3a0189547e1a1f4b4566e1d4d39
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253171B2
Reaction notes
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