tert-Butyl bromoacetate → (S)-N-[[3-[[(t-Butyloxy)carbonyl]amino]-2-oxo-1-azetidinyl]carbonyl]glycine, t-butyl ester
Reaction equation
[O-:1][C:2]#[N:3].[K+].Br[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:14]([O:18][C:19]([NH:21][C@H:22]1[CH2:25][NH:24][C:23]1=[O:26])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([O:18][C:19]([NH:21][C@H:22]1[CH2:25][N:24]([C:2]([NH:3][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:1])[C:23]1=[O:26])=[O:20])([CH3:17])([CH3:15])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of potassium cyanate (933 mg, 11.5 mmol) in 10 ml of dimethylformamide was added t-butyl bromoacetate (1.8 ml, 11 mmol). The mixture was heated to 100° C. for 1 hour and cooled to room temperature. (S)-3-[[(t-Butyloxy)carbonyl]amino]-2-azetidinone (1.860 g, 10 mmol) was then added, and the mixture was heated to 65° C. After being stirred at 65° C. for 1 hour, the mixture was heated to 100° C. and stirred for an additional hour. Additional isocyanate was prepared (using 933 mg of potassium cyanate and 1.8 ml of t-butyl bromoacetate as described above) and added to the reaction mixture at room temperature. After being heated at 65° C. for 1 hour and 100° C. for 1 hour, the reaction mixture was stirred at room temperature overnight.
Workup
- temperaturecooled to room temperature
- temperaturethe mixture was heated to 65° C
- temperaturethe mixture was heated to 100° C.
- stirringstirred for an additional hour
- additionadded to the reaction mixture at room temperature
- temperatureAfter being heated at 65° C. for 1 hour and 100° C. for 1 hour
- stirringthe reaction mixture was stirred at room temperature overnight
Sources & evidence
- ORD record
- ord-74cfddbd1f5149ca843ebe085300059b
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04576749
Reaction notes
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