HCID 19735042, compound → HCID 19735037, compound

HRID 326725Notes

Reaction equation

HRID 326725 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH:13]([CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19735042HCID 19735042, compound

Product 1

HCID 19735037HCID 19735037, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(N-benzyloxycarbonyl-4-oxo-isoxazol-5-yl)butyric acid (327 mg, 1.06 mmol), from Step b, in 10 mL of THF at 0° C. was added 1.1 mL (2.13 mmol) of a 2M solution of borane-methyl sulfide complex in THF. The reaction mixture was stirred at ambient temperature for 1.5 hours, diluted with ethyl acetate and extracted with water. The aqueous layer was acidified with potassium hydrogen sulfate and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 324 mg of the title compound. MS (DCl/NH3) m/e 294 (M+H)+, 311 (M+NH4)+.

Workup

  1. extractionextracted with water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-516c80441c37467f9278c5005a16b60c
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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