Chlorosuccinimide → 2-(2-Boc-amino-5-chlorothiazol-4-YL)-2-oxoacetic acid
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:18])[C:15]([OH:17])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:26])C(=O)C1>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([Cl:26])=[C:12]([C:14](=[O:18])[C:15]([OH:17])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 40 °C
Procedure
To a suspention of 2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoacetic acid (23.5 g, 86 mmol) in 1,4-Dioxane (200 mL) was added NCS (12.22 g, 91 mmol) portionwise. The mixture was stirred at 40° C. for 2.5 h. The mixture was cooled to r.t. and filtered to remove the insoluable material. The filtrate was concentrated under vacuum. The residue was taken with Et2O and filtered. The filtrate was diluted with EtOAc and washed with water and brine. The organic solution was dried over sodium sulfate, filtered and concentrated. To the oily residue was added n-hexane and Et2O, and the mixture was concentrated in vacuo. After trituration, 2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-oxoacetic acid (22.8 g, 74.3 mmol, 86% yield) was obtained as a light yellow solid. LCMS: (M+Na)+: 329.0.
Workup
- temperatureThe mixture was cooled to r.t.
- filtrationfiltered
- customto remove the insoluable material
- concentrationThe filtrate was concentrated under vacuum
- filtrationfiltered
- additionThe filtrate was diluted with EtOAc
- washwashed with water and brine
- dry with materialThe organic solution was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- additionTo the oily residue was added n-hexane and Et2O
- concentrationthe mixture was concentrated in vacuo
Sources & evidence
- ORD record
- ord-ec33daea60214f6bbcd1f49d80952e4b
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340556B2
Reaction notes
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