Hydrochloric Acid → Ethyl cyano-[[[2'-[[[(propylamino)-carbonyl]-amino]-sulfonyl]-(1,1'-biphenyl)-4-yl]-methyl]-(1-oxopentyl)-amino]-acetate

HRID 260547Notes

Reaction equation

HRID 260547 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([NH2:31])(=[O:30])=[O:29])=[CH:18][CH:17]=1)[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])[C:6]#[N:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:39]([N:42]=[C:43]=[O:44])[CH2:40][CH3:41].Cl>CC(C)=O.ClCCl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:6]#[N:7])[N:8]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([NH:31][C:43]([NH:42][CH2:39][CH2:40][CH3:41])=[O:44])(=[O:29])=[O:30])=[CH:20][CH:21]=1)[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61033Propyl isocyanateHCID 131719438Ethyl[[[2'-(aminosulfonyl)-(1,1'-biphenyl)-4-yl]-methyl]-(1-oxopentyl)-amino]-cyanoacetate

Product 1

HCID 54501917Ethyl cyano-[[[2'-[[[(propylamino)-carbonyl]-amino]-sulfonyl]-(1,1'-biphenyl)-4-yl]-methyl]-(1-oxopentyl)-amino]-acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

7.2 g of the product of Stage A, 6.5 g of anhydrous potassium carbonate and 1.48 ml of n-propyl isocyanate were stirred in 180 ml of acetone at reflux for 2 hours 30 minutes. After cooling, the solution was treated with 2N hydrochloric acid and the residue obtained was dissolved in an aqueous mixture of dichloromethane. After extraction with methylene chloride, the extracts were dried and the solvents were eliminated under reduced pressure and the product was crystallized from ethyl acetate to obtain 6.5 g of the expected product as a white solid with a Rf (SiO2, ethyl acetate)=0.48 and melting at 131°-133° C.

Workup

  1. temperatureat reflux for 2 hours 30 minutes
  2. temperatureAfter cooling
  3. customthe residue obtained
  4. extractionAfter extraction with methylene chloride
  5. customthe extracts were dried
  6. customthe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3083ec4d502b4298bcb64328b4705a2a
Source dataset
uspto-grants-1996_06
Patent number
US05527919

Reaction notes

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