Methanesulfonic Acid → HCID 67607702, compound
Reaction equation
[Cl:1][CH2:2][C@@H:3]([OH:21])[CH2:4][C@@H:5]([OH:20])[CH2:6][C:7]([O:9][C:10]([CH3:19])([CH3:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8].CO[C:24](OC)([CH3:26])[CH3:25].CS(O)(=O)=O>CC(C)=O.C(OCC)(=O)C>[Cl:1][CH2:2][C@H:3]1[O:21][C:24]([CH3:26])([CH3:25])[O:20][C@@H:5]([CH2:6][C:7]([O:9][C:10]([CH3:18])([CH3:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:4]1Participants
6
Procedure
The crude compound (3R,5S)-2-methyl-1-phenylpropan-2-yl 6-chloro-3,5-dihydroxy-hexanoate (21.1 g) prepared in Example 3 was dissolved in acetone (210 ml), and 2,2-dimethoxypropane (65.6 ml) and methanesulfonic acid (0.2 ml) were added dropwise thereto, followed by stirring at room temperature for 2 hours. The reaction liquid was diluted with ethyl acetate (320 ml) and washed successively with a saturated sodium bicarbonate aqueous solution (320 ml), a saturated sodium chloride aqueous solution (320 ml) and purified water (320 ml). The separated organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give the crude title compound (23.7 g).
Workup
- customThe reaction liquid
- washwashed successively with a saturated sodium bicarbonate aqueous solution (320 ml)
- customa saturated sodium chloride aqueous solution (320 ml) and purified water (320 ml)
- dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-75bf7b91bafb4ff98600ac0857b9c07d
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524914B2
Reaction notes
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