Water → Ethyl cyano-[[[2'-[[[(dimethylamino)methylene]amino]sulfonyl](1,1'-biphenyl)4-yl]methyl](1-oxopentyl)amino]acetate

HRID 260549Notes

Reaction equation

HRID 260549 reaction equation
[NH2:1][C:2](SC)=[C:3]([N:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([NH:32][C:33]([NH:35][CH2:36]CC)=O)(=[O:31])=[O:30])=[CH:19][CH:18]=1)[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([O:6][CH2:7][CH3:8])=[O:5].O.[CH3:42]OC>C(O)CO.S(=O)(=O)(O)O>[C:2]([CH:3]([N:9]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[S:29]([N:32]=[CH:33][N:35]([CH3:36])[CH3:42])(=[O:30])=[O:31])=[CH:21][CH:22]=1)[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:1]

Participants

6

Reactant 3

HCID 962WaterHCID 8254Dimethyl EtherHCID 67741886Ethyl 3-amino-2-[[[2'-[[[(propylamino)-carbonyl]-amino]sulfonyl]-(1,1'-biphenyl)-4-yl]-methyl]-(1-oxopentyl)-amino]-3-(methylthio)-2-propenoate

Product 1

HCID 53759157Ethyl cyano-[[[2'-[[[(dimethylamino)methylene]amino]sulfonyl](1,1'-biphenyl)4-yl]methyl](1-oxopentyl)amino]acetate

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 1118Sulfuric AcidSolvent

Procedure

200 mg of the product of Stage C of Example 3 were dissolved in 5 ml of dimethyl ether of ethylene glycol and 1 ml of concentrated sulfuric acid was added at ambient temperature. After stirring for one hour, water was added while cooling in an ice bath. Extraction was carried out with dichloromethane and the organic phases .were washed and dried. The solvent was evaporated under reduced pressure to obtain 180 mg of crude product which was crystallized from ethyl acetate to obtain 140 mg of the expected product melting at 130°-132° C.

Workup

  1. additionwas added at ambient temperature
  2. temperaturewhile cooling in an ice bath
  3. extractionExtraction
  4. washthe organic phases .were washed
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customto obtain 180 mg of crude product which
  8. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9d6528f1b5d2408c8239e2f067ec4f57
Source dataset
uspto-grants-1996_06
Patent number
US05527919

Reaction notes

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