1,1-Dichloroethane → HCID 70011773, compound

HRID 1369059Notes

Reaction equation

HRID 1369059 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18](O)=[O:19])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].ON1C2N=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.ClC(Cl)C.[CH2:50]([NH:57][CH:58]1[C:67]2[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=2)[CH2:61][CH2:60][CH:59]1[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([O:75][CH3:76])[CH:70]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C)C1C=CN=CC=1.ClCCl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18](=[O:19])[N:57]([CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:58]3[C:67]4[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=4)[CH2:61][CH2:60][CH:59]3[CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[C:71]([O:75][CH3:76])[CH:70]=3)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

9

Reactant 5

HCID 63651,1-DichloroethaneHCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 18517959HCID 18517959, compoundHCID 20592441HCID 20592441, compound

Product 1

HCID 70011773HCID 70011773, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3′-Carboxymethyl-biphenyl-3-carboxylic acid methyl ester (77 mg) is combined with 76 mg 1-hydroxy-7-azabenzotriazole, 234 mg polymer-bound DCC, and 4 mg 4-dimethylaminopyridine in 4 ml 3:1 dichloroethane:DMF. The slurry is shaken 30 minutes at ambient temperature before adding 100 mg Benzyl-[2-(3-methoxy-benzyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-amine (prepared in a similar fashion to Preparation C). The mixture is shaken at ambient temperature 18 hours. The resin is filtered off and washed with dichloromethane and methanol. The solvent is evaporated to give a yellow oil. The oil is dissolved in dichloromethane, the insoluble material is filtered off, and the filtrate is separated by radial chromatography (4 mm plate, 3:1 hexanes:ethyl acetate). Product fractions are combined and evaporated to give 76 mg of the title compound as a colorless oil, 42%.

Workup

  1. customprepared in a similar fashion to Preparation C)
  2. stirringThe mixture is shaken at ambient temperature 18 hours
  3. filtrationThe resin is filtered off
  4. washwashed with dichloromethane and methanol
  5. customThe solvent is evaporated
  6. customto give a yellow oil
  7. filtrationthe insoluble material is filtered off
  8. customthe filtrate is separated by radial chromatography (4 mm plate, 3:1 hexanes:ethyl acetate)
  9. customevaporated

Sources & evidence

ORD record
ord-c3e0d43c2ac447e7a6f16fe17754d27d
Source dataset
uspto-grants-2003_06
Patent number
US06576632B1

Reaction notes

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