Water → HCID 69338454, compound

HRID 2086204Notes

Reaction equation

HRID 2086204 reaction equation
C(OC(NC(OC(=O)CCCCC)[C@H](C)[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[CH:21]=1)=O)(C)(C)C.[OH-:31].[Na+].C[C:34]([CH3:37])([O-])[CH3:35].[K+].O.C[N:41](C)[CH:42]=[O:43]>O1CCCC1.CO>[S:18]1[CH:19]=[CH:20][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][N:41]3[C@H:34]([CH3:37])[CH2:35][O:31][C:42]3=[O:43])=[CH:21][C:17]1=2

Participants

8

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 20721235HCID 20721235, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69338454HCID 69338454, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R)-t-Butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(benzo[b]thiophen-6-yl)butane (24.3 g, 56.0 mmol) obtained in Example 68(b) was dissolved in a mixture of tetrahydrofuran (220 ml) and methanol (110 ml), and a 1N aqueous sodium hydroxide solution (110 ml) was added thereto in an ice bath followed by stirring for 15 minutes in the ice bath and subsequently for 2 hours at room temperature. After the reaction solution was concentrated in vacuo, water was added thereto, and the solution was extracted with dichloromethane, and then the dichloromethane layer was washed with a saturated aqueous sodium chloride solution. The dichloromethane layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacua to give a crude product (18.8 g, 100% yield). This crude product was dissolved in dimethylformamide (380 ml), and potassium t-butoxide (9.43 g, 84.1 mmol) was added thereto in an ice bath followed by stirring for 5 minutes in the ice bath and subsequently for 1 hour at room temperature. To the reaction solution was added water, and the resulting solution was extracted with ethyl acetate, and then the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:2-2:1) to afford the title compound (13.8 g, 94% yield) as a white solid.

Workup

  1. customin an ice bath followed
  2. concentrationAfter the reaction solution was concentrated in vacuo, water
  3. additionwas added
  4. extractionthe solution was extracted with dichloromethane
  5. washthe dichloromethane layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated in vacua
  8. customto give a crude product (18.8 g, 100% yield)
  9. customin an ice bath followed
  10. extractionthe resulting solution was extracted with ethyl acetate
  11. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  12. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  13. customthe solvent was evaporated under reduced pressure
  14. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=3:2-2:1)

Sources & evidence

ORD record
ord-a4272ba9258a4a5eac77c70fcc297e4a
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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