Dicyclohexylcarbodiimide → HCID 86660332, compound

HRID 469495Notes

Reaction equation

HRID 469495 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]([C:15]1[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:12]([OH:14])=[O:13])=[O:4].C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1.[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50](O)[CH2:49]2>C1COCC1>[CH3:22][O:21][C:18]1[N:17]=[CH:16][C:15]([C@@H:11]([NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[C:12](=[O:14])[O:13][CH:50]2[CH:51]3[CH2:54][CH2:55][N:48]([CH2:53][CH2:52]3)[CH2:49]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58556932HCID 58556932, compound

Product 1

HCID 86660332HCID 86660332, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I59) (548 mg, 1.70 mmol) in THF (20 ml), were added N,N′-methanediylidenedicyclohexanamine (421 mg, 2.04 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (276 mg, 2.04 mmol), and (R)-quinuclidin-3-ol (259 mg, 2.04 mmol). The reaction mixture was stirred at room temperature for 15 hours, and then the solvent was evaporated. The residue was taken up with DCM, and the insoluble was removed by filtration. The organic phase was washed twice with Na2CO3 and then brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH=95/5) collecting first diastereomer 1 of C60 (140 mg, 19 yield) and then a mixture of diastereomers 1 and 2 of C60 (100 mg, 14% yield).

Workup

  1. customthe solvent was evaporated
  2. customthe insoluble was removed by filtration
  3. washThe organic phase was washed twice with Na2CO3
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (DCM/MeOH=95/5)
  8. customcollecting first
  9. customdiastereomer 1 of C60 (140 mg, 19 yield)
  10. additiona mixture of diastereomers 1 and 2 of C60 (100 mg, 14% yield)

Sources & evidence

ORD record
ord-1b551024da4b4c4180dc01a99e339072
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

Loading…