Water → HCID 20721247, compound
Reaction equation
C(OC(N[CH:9]([OH:19])[C@H:10](C)[CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=O)(C)(C)C.CC(C)([O-])C.[K+].O.[CH3:27][N:28](C)[CH:29]=[O:30]>>[CH3:27][N:28]1[C@H:10]([CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:19][C:29]1=[O:30]Participants
Procedure
(2R)-t-Butoxycarbonylamino-2-methyl-4-(thiophen-2-yl)-1-butanol (15.4 g, 53.9 mmol) obtained in Example 67(b) was dissolved in N,N-dimethylformamide (200 ml), and potassium t-butoxide (9.07 g, 80.8 mmol) was added thereto in an ice bath followed by stirring for 10 minutes in an ice bath and subsequently for 40 minutes at room temperature. To the reaction solution was added water, and then the solution was extracted with ethyl acetate, and after the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:1) to afford the title compound (11.5 g, 100% yield) as a white solid. The data obtained from analytical instruments were in accord with that obtained in Example 66.
Workup
- customin an ice bath followed
- extractionthe solution was extracted with ethyl acetate
- washafter the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated in vacuo
- customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:1-1:1)
Sources & evidence
- ORD record
- ord-27923e09693f49448306efc8d9201040
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06964976B2
Reaction notes
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