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

HRID 260550Notes

Reaction equation

HRID 260550 reaction equation
[C:1]([CH:3]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([NH:26][C:27]([NH:29][CH2:30][CH2:31][CH3:32])=[O:28])(=[O:25])=[O:24])=[CH:13][CH:12]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])([O-])=O.[K+].[K+].[C:39](Cl)(=[O:44])[CH2:40][CH2:41][CH2:42][CH3:43]>CC(C)=O>[C:1]([CH:3]([N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23]([NH:26][C:27]([NH:29][CH2:30][CH2:31][CH3:32])=[O:28])(=[O:25])=[O:24])=[CH:15][CH:16]=1)[C:39](=[O:44])[CH2:40][CH2:41][CH2:42][CH3:43])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61186Valeryl chlorideHCID 11102546Ethyl cyano-[[[2'-[[[(propylamino)-carbonyl]-amino]-sulfonyl]-(1,1'-biphenyl)-4-yl]-methyl]-amino]-acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.7 g of the product of Stage A were dissolved in 50 ml of acetone and 0.79 g of K2CO3 and 0.45 ml of valeryl chloride were added. The mixture was stirred for 6 hours at ambient temperature and the insoluble part was filtered. The filtrate was evaporated to dryness, which after purification by chromatography (eluant: dichloromethane-ethyl acetate 4-1) yielded 295 mg of the expected product with a Rf (SiO2, dichloromethane ethyl acetate 4-1)=0.30.

Workup

  1. filtrationthe insoluble part was filtered
  2. customThe filtrate was evaporated to dryness, which
  3. customafter purification by chromatography (eluant: dichloromethane-ethyl acetate 4-1)

Sources & evidence

ORD record
ord-31a46e48db784f86828d57062d7ae3b1
Source dataset
uspto-grants-1996_06
Patent number
US05527919

Reaction notes

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