Reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:3]1.[C:15]([NH:25][CH2:26][C:27](O)=[O:28])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:19]1([CH2:18][O:17][C:15](=[O:16])[NH:25][CH2:26][C:27]([NH:1][N:2]2[CH:6]=[CH:5][C:4]([C:7](=[O:8])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:3]2)=[O:28])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (1-amino-1H-pyrrol-3-yl)phenylmethanone (5.96 g) and N-carbobenzyloxyglycine (6.69 g) in 70 ml of anhydrous DCM and 30 ml of anhydrous dimethylformamide was added DCC (7.22 g). The reaction mixture was stirred at room temperature for 4 hours and filtered. The filter cake was washed with ethyl acetate, and the combined filtrates were evaporated in vacuo. The residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1). Evaporation of the desired fractions afforded a colorless oil, which was crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.
Workup
- filtrationfiltered
- washThe filter cake was washed with ethyl acetate
- customthe combined filtrates were evaporated in vacuo
- customThe residual oil was purified by preparative HPLC (silica gel, DCM/ethyl acetate 3:1)
- customEvaporation of the desired fractions
- customafforded a colorless oil, which
- customwas crystallized from DCM/ethyl ether yielding the product as colorless crystals (5.96 g), m.p. 144°-145° C.
Sources & evidence
- ORD record
- ord-28bfdfd39e0b4541807aad6bd92012f7
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576446
Linked notes
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