Dimethyl Sulfoxide → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate
Reaction equation
CS(C)=O.[C:5]([NH:12][C@H:13]([CH2:18][OH:19])[CH2:14][CH:15]([CH3:17])[CH3:16])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CCN(CC)CC>C(Cl)Cl>[C:5]([NH:12][C@H:13]([CH:18]=[O:19])[CH2:14][CH:15]([CH3:16])[CH3:17])([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A solution of sulfur trioxide pyridine complex (7.8 g, 49.1 mmol, 3.0 equiv) in a 1:1 mixture of DMSO and CH2Cl2 (100 mL) was added to a solution of BOC-L-Leucinol (3.56 g, 16.4 mmol. 1 equiv) and Et3N (8 mL) in a 1:1 mixture of DMSO and CH2Cl2 (100 mL) at 0° C. The reaction mixture was stirred at 23° C. for 30 min, then poured into ice water (300 mL), and extracted with Et2O (2×200 mL). The combined organic layers were washed with 0.5 M HCl (150 mL), half saturated NaHCO3 (150 mL) and H2O (2×150 mL), then dried over Na2SO4, and concentrated to afford crude BOC-L-Leucinal as pale yellow oil (3.48 g, 99%). This material was used without further purification. 1H NMR (CDCl3) δ 0.92-0.94 (m, 6H), 1.44 (s, 9H), 1.59-1.64 (m, 1H), 1.67-1.85 (m, 2H), (4.21 (m, 1H), 5.12 (s, br, 1H), 9.57 (s, 1H).
Workup
- extractionextracted with Et2O (2×200 mL)
- washThe combined organic layers were washed with 0.5 M HCl (150 mL), half saturated NaHCO3 (150 mL) and H2O (2×150 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2abce9628d78499bbc19d1a11fc336d8
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06331554B1
Reaction notes
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