Water → HCID 20721214, compound

HRID 2086199Notes

Reaction equation

HRID 2086199 reaction equation
[NH2:1][CH:2]([OH:24])[C@H:3]([CH3:23])[CH2:4][CH2:5][C:6]1[S:7][C:8]([C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:10]=1.[BH4-].[Na+].O.[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>CO>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[NH2:1][CH:2]([OH:24])[C@H:3]([CH3:23])[CH2:4][CH2:5][C:6]1[S:7][C:8]([CH:11]([OH:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 20721231HCID 20721231, compound

Product 1

HCID 20721214HCID 20721214, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R)-Amino-2-methyl-4-[5-(5-phenylpentanoyl)thiophen-2-yl]butan-1-ol (130 mg, 0.38 mmol) obtained in Example 50 was dissolved in methanol (3 ml), and sodium borohydride (17 mg, 0.45 mmol) was added thereto in an ice bath followed by stirring for 1 hour at room temperature. To the reaction solution was added water in the ice bath, and the resulting solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol, and oxalic acid (34 mg, 0.38 mmol) was added thereto, and the solvent was evaporated in vacuo. To the residue was added ethanol (3 ml), and the resulting precipitate was filtered off to give the title compound (95 mg, 58% yield) as a white crystalline solid.

Workup

  1. customin an ice bath followed
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in methanol
  7. customthe solvent was evaporated in vacuo
  8. additionTo the residue was added ethanol (3 ml)
  9. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-f9d756ce00b948b4b96b223954c07ca4
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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