4-Toluenesulfonyl chloride → (S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl 4-methylbenzenesulfonate
Reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][O:10][S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:18])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The recovered intermediate (20a) (8.5 g, 33 mmol, 1.0 eq) was dissolved into 70 mL pyridine containing potassium hydroxide (2.1 g, 37 mmol, 1 . 1 eq) and the mixture was chilled in an ice bath. Tosyl chloride (7.1 g, 37 mmol, 1.1 eq) was added and the mixture was stirred at 0° C. for 2 hours then refrigerated overnight. The mixture was filtered and the filtrate was concentrated under reduced pressure. The recovered residue was dissolved into 300 mL EtOAc, washed with 2×200 mL 1M H3PO4, saturated bicarbonate, and saturated aqueous NaCl. The organic was dried over MgSO4 and concentrated under reduced pressure to yield intermediate (20b) (10.3 g) as a pale brown oil.
Workup
- temperaturethe mixture was chilled in an ice bath
- waitthen refrigerated overnight
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- dissolutionThe recovered residue was dissolved into 300 mL EtOAc
- washwashed with 2×200 mL 1M H3PO4, saturated bicarbonate, and saturated aqueous NaCl
- dry with materialThe organic was dried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9608ac7b72eb415ab4b48b3c9278be2f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012485B2
Reaction notes
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