Allyl bromide → Benzyl allyl(2,2-dimethoxyethyl)carbamate
Reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:18](Br)[CH:19]=[CH2:20].[OH-].[Na+]>C1(C)C=CC=CC=1.[Cl-].C[N+](CCCC)(CCCC)CCCC>[CH2:20]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:16][CH3:17])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:19]=[CH2:18]Participants
6
Conditions
- Temperature
- 16 °C
Procedure
The solution of Example 4A in toluene (343 Kg) was charged to a 200-gallon reactor followed by addition of allyl bromide (41.5 Kg) and methyltributylammonium chloride (8.3 Kg). The mixture was stirred for 15 minutes, cooled to 16° C., and treated with 50% NaOH solution (296.9 Kg) slowly over 1 hour while maintaining the internal temperature below 30° C. The mixture was stirred at room temperature until there remained no more than 1.0% 1, as determined by HPLC. The mixture was allowed to settle and the layers were separated. The organic layer was washed with phosphate buffer solution made of 10 mM KH2PO4 and 10 mM K2HPO4 (2×260 Kg), followed by a water wash (256 Kg).
Workup
- temperaturewhile maintaining the internal temperature below 30° C
- stirringThe mixture was stirred at room temperature until there
- customthe layers were separated
- washThe organic layer was washed with phosphate buffer solution
- washwash (256 Kg)
Sources & evidence
- ORD record
- ord-c740aad84a644a7b8f32246156b14223
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498444B2
Reaction notes
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