4-Methylmorpholine → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester
Reaction equation
N([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H](C(N[C@@H](C(OC)=O)CCC(=O)O)=O)C.C([CH2:31][C@H:32]([NH2:36])[C:33]([OH:35])=[O:34])C[C@@H](N)C(O)=O.N[CH2:38][C:39]([OH:41])=O.ClC1C=CC(S(ON2C3C=C(Cl)C=[CH:61][C:56]=3[N:55]=N2)(=O)=O)=CC=1.CN1CC[O:67]CC1>C(Cl)Cl>[NH:36]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@@H:32]([C:33]([O:35][N:55]1[C:39](=[O:41])[CH2:38][CH2:61][C:56]1=[O:67])=[O:34])[CH3:31]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-54e9aee8845b4a6caf290d859a69fadb
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04458078
Reaction notes
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