Sodium Hydroxide → HCID 69338807, compound

HRID 1063459Notes

Reaction equation

HRID 1063459 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([O:19]C(=O)CCCCC)[C@H:10]([CH3:18])[CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1.CO>[C:1]([O:5][C:6]([NH:8][CH:9]([OH:19])[C@H:10]([CH3:18])[CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20721237HCID 20721237, compound

Product 1

HCID 69338807HCID 69338807, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R)-t-Butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-2-yl)butane (22.0 g, 57.4 mmol) obtained in Example 67(a) was dissolved in a mixture solution of tetrahydrofuran (140 ml) and methanol (280 ml), and a 1N aqueous sodium hydroxide solution (280 ml) was added in an ice bath followed by stirring 30 minutes in an ice bath and subsequently for 1 hour at room temperature. The reaction solution was concentrated in vacuo, and water was added thereto, and after the resulting solution was extracted with dichloromethane, 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 vacuo to afford the title compound (15.5 g, 95% yield) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo, and water
  2. additionwas added
  3. extractionafter the resulting solution was extracted with dichloromethane
  4. washthe dichloromethane layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d40ce5ad582049d389ca00514e8e07d7
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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