p-Toluenesulfonyl azide → Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([N:38]=[N+:39]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)[C:9]1[S:10][CH:11]=[C:12]([C:14](=[N+:38]=[N-:39])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]acetate (synthesized as per preparation 44; 3.8 g, 9.35 mmol) in dry acetonitrile was added para-toluene sulfonyl azide (2.04 g, 10.3 mmol) followed by DBU (2.09 mL, 14.0 mmol) in dropwise manner. The reaction stirred for 30 min. then poured in ice cold water (20 mL) extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide crude product, which was purified by column chromatography using 5-7% ethyl acetate in hexane to afford Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate (3.3 g).
Workup
- extractionextracted with ethyl acetate (3×20 mL)
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customto provide crude product, which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-b20995f64fb84dfe9fbaf92016e5ee14
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340506B2
Reaction notes
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