Phosgene → N-[N-(1-Carboxy-3-phenylpropyl)-alpha-azaglycinyl]-4(R)carboethoxy-2-(2-hydroxyphenyl)thiazolidine
Reaction equation
[C:1](Cl)(Cl)=[O:2].FC(F)(F)C(O)=O.[C:12]1([CH2:18][CH2:19][CH:20]([NH:26][NH2:27])[C:21]([O:23]CC)=[O:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[C:35]([C@@H:40]1[CH2:44][S:43][CH:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[OH:51])[NH:41]1)([O:37][CH2:38][CH3:39])=[O:36]>C(Cl)Cl>[C:21]([CH:20]([NH:26][NH:27][C:1]([N:41]1[C@H:40]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:44][S:43][CH:42]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[OH:51])=[O:2])[CH2:19][CH2:18][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:23])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
An ice-cold solution of phosgene (1.1 M solution in toluene; 0.91 ml) was diluted with CH2Cl2 (3 ml) and then a solution of 56 (0.34 g, 1.0 mmol) and triethylamine (0.28 ml; 2.0 mmol) in CH2Cl2 (3 ml) was added slowly with cooling (ice-bath). Then a solution of 57 (0.25 g; 1.0 mmol) and triethyl amine (0.14 ml; 1.0 mmol) in CH2Cl2 (3 ml) was added and stirring was continued at room temperature for 6 hours. The reaction mixture was diluted with EtAc (25 ml) and extracted with H2O (2×10 ml) and brine, and dried (MgSO4). The residue after evaporation was subjected to chromatography on silica gel, allowing isolation of 58.
Workup
- temperaturewith cooling (ice-bath)
- additionThe reaction mixture was diluted with EtAc (25 ml)
- extractionextracted with H2O (2×10 ml) and brine
- dry with materialdried (MgSO4)
- customThe residue after evaporation
Sources & evidence
- ORD record
- ord-29a584bcb1b84508a98d4a90b9654777
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04634715
Reaction notes
Loading…