Tributylstannane → BENZYL 4-OXO-2-[[(PHENYLMETHOXY)CARBONYL]AMINO]BUTANOATE

HRID 1444678Notes

Reaction equation

HRID 1444678 reaction equation
[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][C:4](=O)[OH:5].C(Cl)(=O)C(Cl)=O.C([SnH](CCCC)CCCC)CCC>CN(C=O)C>[CH2:10]([O:9][C:7](=[O:8])[CH:2]([NH:1][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[CH2:3][CH:4]=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 65578Oxalyl chlorideHCID 6994509Z-Asp-OBzl

Product 1

HCID 11359778BENZYL 4-OXO-2-[[(PHENYLMETHOXY)CARBONYL]AMINO]BUTANOATE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Z-Asp-OBn (10 g, 0.028 mol) in MC (200 ml), oxalyl chloride (2.93 ml, 0.0336 mol) and a catalytic amount of DMF were added at 0° C. and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was dissolved in benzene (400 ml), and tributyltin hydride (15.1 ml, 0.056 mol) and a catalytic amount of Pd(0) were added slowly at 0° C. and stirred at room temperature overnight. After the solvent was evaporated, ether (100 ml)/10% KF in water (100 ml) was added and stirred at room temperature for 2 hrs, followed by filtration to give a biphasic solution. The organic layer was separated and concentrated to give a crude product, which was purified by column chromatography to obtain the title compound, Z-Asp-OBn aldehyde (6 g) as pale-yellow oil.

Workup

  1. customAfter the solvent was evaporated
  2. dissolutionthe crude acyl chloride was dissolved in benzene (400 ml)
  3. stirringstirred at room temperature overnight
  4. customAfter the solvent was evaporated
  5. additionether (100 ml)/10% KF in water (100 ml) was added
  6. stirringstirred at room temperature for 2 hrs
  7. filtrationfollowed by filtration
  8. customto give a biphasic solution
  9. customThe organic layer was separated
  10. concentrationconcentrated
  11. customto give a crude product, which
  12. customwas purified by column chromatography

Sources & evidence

ORD record
ord-94edc024db3f49ccad71ef43ff1c1247
Source dataset
uspto-grants-2010_02
Patent number
US07662960B2

Reaction notes

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