3-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester → 3-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

HRID 1824436Notes

Reaction equation

HRID 1824436 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15](=[O:27])[CH2:16][CH:17]([NH:20][C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH:18]=[O:19])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15](=[O:27])[CH2:16][CH:17]([NH:20][C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH:18]([OH:19])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 184657153-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl esterHCID 178418336HCID 178418336, compound

Product 1

HCID 235714393-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of benzylmagnesium chloride (20 mL, 20 mmol) in THF at −78° C. is added dropwise a 0° C. solution of 3-allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester, 102, (5.14 g, 20 mmol) in THF (100 mL). Once the addition is complete, the solution is allowed to warm to 0° C. over 30 minutes then the reaction mixture is poured into a beaker of crushed ice. The solution is extracted ×3 with CH2Cl2 (100 mL), the organic layers combined, dried over Na2SO4 and concentrated in vacuo to afford the desired product which is used without further purification.

Workup

  1. additionOnce the addition
  2. additionthe reaction mixture is poured into a beaker of crushed ice
  3. extractionThe solution is extracted ×3 with CH2Cl2 (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05a39716b91042c7ade495519a27e997
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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