Water → HCID 20721247, compound

HRID 2086202Notes

Reaction equation

HRID 2086202 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

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23665647Potassium tert-butoxideHCID 69338807HCID 69338807, compound

Product 1

HCID 20721247HCID 20721247, compoundYield 100%

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 tide 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

  1. customin an ice bath followed
  2. extractionthe solution was extracted with ethyl acetate
  3. washafter the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. 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-48b2b2e1e6ad42d4bd1e7bbc9d673cab
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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