Water → (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate
Reaction equation
[C:1]([O:4][CH2:5][CH:6]([OH:23])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:4][CH2:5][C@@H:6]([O:23][S:32]([CH3:31])(=[O:34])=[O:33])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °C
Procedure
To a suitable reactor was added 4a (2 g, 6.18 mmol), CH2Cl2 (20 mL), DMAP (0.15 g, 1.24 mmol), and Et3N (1.37 g, 13.61 mmol) at 20-30° C. under N2. The mixture was cooled to 0-5° C., and MsCl (1.4 g, 12.36 mmol) in CH2Cl2 (3 mL) solution was added at this temperature. The mixture was warmed to 20-30° C. and stirred for 1 hr. H2O (10 mL) was added at 20-30° C., and the mixture was stirred at this temperature for 30 min. The separated organic portion was washed with 20% NaCl aqueous solution (10 mL). The separated organic portion was concentrated at 40-50° C. under reduced pressure to afford 5 (2.8 g) as a yellow solid in quantitative yield.
Workup
- temperatureThe mixture was warmed to 20-30° C.
- stirringthe mixture was stirred at this temperature for 30 min
- washThe separated organic portion was washed with 20% NaCl aqueous solution (10 mL)
- concentrationThe separated organic portion was concentrated at 40-50° C. under reduced pressure
Sources & evidence
- ORD record
- ord-3c6d419db57947afb94d9f1332370bd2
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722921B2
Reaction notes
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