Diisopropylethylamine → HCID 86726297, compound

HRID 1422880Notes

Reaction equation

HRID 1422880 reaction equation
[NH2:1][C@H:2]([C:12](=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9](=[O:11])[CH3:10].FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[O:70]=[C:71]1[C@H:75]([C:76](O)=[O:77])[C@@H:74]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:73][NH:72]1>C(Cl)Cl.CN(C=O)C>[O:70]=[C:71]1[CH:75]([C:76]([NH:1][C@H:2]([C:12](=[O:20])[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9](=[O:11])[CH3:10])=[O:77])[CH:74]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:73][NH:72]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 762604HCID 762604, compoundHCID 2724699PyBOPHCID 86726298HCID 86726298, compound

Product 1

HCID 86726297HCID 86726297, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Thioacetic acid S—((S)-6-amino-6-phenylcarbamoyl-hexyl) ester-trifluoroacetate (1.03 mmol), DIPEA (3.08 mmol) and PyBOP (1.03 mmol) were added to a solution of (3R*,4S*)-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid in DCM/DMF: 5/9. The resulting reaction mixture was stirred at RT overnight. After removal of the solvent under reduced pressure, the resulting solid was poured into water and extracted twice with AcOEt. The organic layer was then washed with NaHCO3, water and brine before being dried over Na2SO4 and concentrated under reduced pressure to yield an oil. The latter was partially purified by silica gel chromatography and then subjected to HPLC purification.

Workup

  1. customThe resulting reaction mixture
  2. customAfter removal of the solvent under reduced pressure
  3. additionthe resulting solid was poured into water
  4. extractionextracted twice with AcOEt
  5. washThe organic layer was then washed with NaHCO3, water and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto yield an oil
  9. customThe latter was partially purified by silica gel chromatography
  10. customsubjected to HPLC purification

Sources & evidence

ORD record
ord-7fe0b12d0a7346b9ae8286c1b01efb0e
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

Loading…