Acetic Acid → Ethyl 3-amino-3-(3-{[(3-{[(propylamino)carbonyl]amino}phenyl)sulfonyl]amino}phenyl)propanoate

HRID 968472Notes

Reaction equation

HRID 968472 reaction equation
C(O)(=O)C.C([SnH](CCCC)CCCC)CCC.C(OC([NH:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH:38][S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([NH:48][C:49]([NH:51][CH2:52][CH2:53][CH3:54])=[O:50])[CH:43]=2)(=[O:41])=[O:40])[CH:33]=1)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=O)C=C.C(=O)(O)[O-].[Na+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH:38][S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([NH:48][C:49]([NH:51][CH2:52][CH2:53][CH3:54])=[O:50])[CH:43]=2)(=[O:41])=[O:40])[CH:33]=1)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5948TributylstannaneHCID 516892Sodium BicarbonateHCID 59015659Ethyl 3-{[(allyloxy)carbonyl]amino}-3-(3-{[(3-{[(propylamino)carbonyl]amino}phenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 59015682Ethyl 3-amino-3-(3-{[(3-{[(propylamino)carbonyl]amino}phenyl)sulfonyl]amino}phenyl)propanoateYield 28.5%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

2.57 ml of acetic acid, 5.32 ml of tributyltin hydride and 177 mg of bis(triphenyl phosphine) palladium(II) chloride were added to a solution of 9.58 g of ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-{{3-{[(3-{[(propylamino)-carbonyl]-amino}-phenyl)-sulphonyl]-amino}-phenyl}}-propanoate from Example II.2.g in 245 ml of dichloromethane, and the resultant mixture was stirred at room temperature for 22 h. An aqueous solution of sodium bicarbonate was added, and the mixture was extracted with dichloromethane. After drying the organic phase over magnesium sulphate, the solvent was removed, and the crude product was purified by chromatography on silica gel (dichloromethane/methanol=10:1) to give 2.30 g of the desired compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialAfter drying the organic phase over magnesium sulphate
  3. customthe solvent was removed
  4. customthe crude product was purified by chromatography on silica gel (dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-6f605b57a630433d97bf017a3fda7dc6
Source dataset
uspto-grants-2007_12
Patent number
US07304037B2

Reaction notes

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