L-Pyroglutamic Acid → (S)-2-benzylcarbamoyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
Reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH:16]1[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C:22]([OH:24])=O.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:33](OC([O-])=O)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].C(N(CC)CC)C>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:36]([O:35][C:33]([N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C:22](=[O:24])[NH:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N′-Dicyclohexyl carbodiimide (DCC; 8.2 g, 40 mmol) was added to a solution of pyroglutamic acid (5.16 g, 40 mmol) in dimethylformamide (DMF; 60 ml). The mixture was stirred at room temperature for 2 h and a precipitate formed. Benzylamine (4.8 ml, 44 mmol) was added and the mixture was stirred for 2 h. t-butyl dicarbonate (Boc2O; 9.6 g, 44 mmol), triethylamine (TEA; 6.3 ml, 44 mmol) and 4-dimethylaminopyridine (DMAP; 488 mg, 4 mmol) were added and the mixture was stirred at room temperature for 16 h. The DMF was removed under vacuum and the residue was taken up with water (20 ml) and extracted with dichloromethane (DCM; 3×20 ml). The organic layers were concentrated and the crude product was purified via silica gel chromatography to afford (S)-2-benzylcarbamoyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (2.23 g, 7.0 mmol, 17.5%).
Workup
- customa precipitate formed
- additionwere added
- stirringthe mixture was stirred at room temperature for 16 h
- customThe DMF was removed under vacuum
- extractionextracted with dichloromethane (DCM; 3×20 ml)
- concentrationThe organic layers were concentrated
- customthe crude product was purified via silica gel chromatography
Sources & evidence
- ORD record
- ord-c29b893a97a54d9590df659b272e770b
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829191B2
Reaction notes
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