4-Methylmorpholine → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester
Reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:4](N[C@@H](C(OC)=O)CCC(=O)O)=[O:5])[CH3:3].N(C(OCC1C=CC=CC=1)=O)[C@H](C(N[C@@H](C(OCC1C=CC=CC=1)=O)CC(O[N:37]1[C:42](=[O:43])[CH2:41][CH2:40][C:38]1=[O:39])C(=O)O)=O)C.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=[O:72])=CC=1.CN1CCOCC1>C(Cl)Cl>[NH:1]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@@H:2]([C:4]([O:5][N:37]1[C:42](=[O:43])[CH2:41][CH2:40][C:38]1=[O:39])=[O:72])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of Boc-L-Ala-D-Glu(OH)OMe (1) (1.94 g), L-Lys(ε-Z)-GlyOEt (2)(1.67 g) and 1-(4-chlorobenzenesulfonyloxy)-6-chlorobenzotriazole (1.72 g) in methylene chloride (100 ml) was added N-methylmorpholine (1.01 g) and the mixture was stirred for 2 days at room temperature. The reaction mixture was washed sccessively with 5% aqueous sodium bicarbonate, water, 5% hydrochloric acid and water and dried over magnesium sulfate. After evaporation of the solvent, the resulting crystalline mass was filtered and washed with ether, to give Boc-L-Ala-γ-D-Glu(α-OMe)-L-Lys(ε-Z)-GlyOEt (3)(1.34 g).
Workup
- washThe reaction mixture was washed sccessively with 5% aqueous sodium bicarbonate, water, 5% hydrochloric acid and water
- dry with materialdried over magnesium sulfate
- customAfter evaporation of the solvent
- filtrationthe resulting crystalline mass was filtered
- washwashed with ether
Sources & evidence
- ORD record
- ord-90e8cd14a57c4932bc4bc0bc341b27c2
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539155
Reaction notes
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