Propyl isocyanate → Ethyl 3-{[(allyloxy)carbonyl]amino}-3-(3-{[(3-{[(propylamino)carbonyl]amino}phenyl)sulfonyl]amino}phenyl)propanoate

HRID 968471Notes

Reaction equation

HRID 968471 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH2:2][CH3:3].[CH2:7]([O:10][C:11]([NH:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=2)(=[O:30])=[O:29])[CH:22]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])[CH:8]=[CH2:9]>O1CCOCC1>[CH2:7]([O:10][C:11]([NH:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[O:6])[CH:32]=2)(=[O:30])=[O:29])[CH:22]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 61033Propyl isocyanateHCID 21101498Ethyl 3-allyloxycarbonylamino-3-(3-[3-aminophenylsulphonylamino]-phenyl)-propionate

Product 1

HCID 59015659Ethyl 3-{[(allyloxy)carbonyl]amino}-3-(3-{[(3-{[(propylamino)carbonyl]amino}phenyl)sulfonyl]amino}phenyl)propanoateYield 32.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

9.6 g of propyl isocyanate were added to a solution of 50 g of enantiopure ethyl 3-{[(allyloxy)-carbonyl]-amino}-3-{{3-{[(3-aminophenyl)-sulfonyl]-amino}-phenyl}}-propanoate from fraction 1 from Example II.2.f in 500 ml of dioxane, and the mixture was stirred for 18 h at 50° C. After evaporation of the solvent, 1.5 L of 1 M hydrochloric acid were added, and the solution was extracted with dichloromethane. The organic phase was dried over magnesium sulphate and concentrated. Chromatography on silica gel (dichloromethane/methanol=30:1) yielded 19.1 g of the compound.

Workup

  1. customAfter evaporation of the solvent, 1.5 L of 1 M hydrochloric acid
  2. additionwere added
  3. extractionthe solution was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-92c35bb42187486eb9ca93a1d3ad07d2
Source dataset
uspto-grants-2007_12
Patent number
US07304037B2

Reaction notes

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