4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4,4-dimethyl-pentyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH2:14][OH:15])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:14][O:15][S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:16])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
To a stirred solution of ((S)-1-hydroxymethyl-3,3-dimethyl-butyl)-carbamic acid tert-butyl ester (3.0 g, 13.0 mmol, 1.0 equiv.) in dry pyridine (14.8 mL) was added tosyl chloride (3.7 g, 19.4 mmol, 1.5 equiv) portionwise at 0° C. under nitrogen. After 4 hours of stirring at room temperature, the reaction mixture was extracted with ethyl acetate (200 mL), washed with water (3×200 mL) followed by brine (2×100 mL), and dried over anhydrous sodium sulfate to give a crude residue. The residue was purified by silica gel column chromatography (100-200 mesh) using a gradient of 5-10% ethyl acetate/hexanes to give toluene-4-sulfonic acid(S)-2-tert-butoxycarbonylamino-4,4-dimethyl-pentyl ester (3 g, 60%).
Workup
- extractionthe reaction mixture was extracted with ethyl acetate (200 mL)
- washwashed with water (3×200 mL)
- dry with materialdried over anhydrous sodium sulfate
- customto give a crude residue
- customThe residue was purified by silica gel column chromatography (100-200 mesh)
Sources & evidence
- ORD record
- ord-21aa1eb3133f4d8dbef7e020fab7fb04
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314250B2
Reaction notes
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