Triethylamine → (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoate

HRID 2202559Notes

Reaction equation

HRID 2202559 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:51]([NH:53][CH2:54][C:55]([C:57]1[C:58]([O:67][CH3:68])=[N:59][C:60]2[C:65]([CH:66]=1)=[CH:64][CH:63]=[CH:62][CH:61]=2)=O)=[O:52])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:51]1[O:52][C:55]([C:57]2[C:58]([O:67][CH3:68])=[N:59][C:60]3[C:65]([CH:66]=2)=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:54][N:53]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][C:47]([CH3:49])([CH3:48])[CH3:50])=[O:45])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 90119771(S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-8-((2-(2-methoxyquinolin-3-yl)-2-oxoethyl)amino)-8-oxooctanoate

Product 1

HCID 90119905(S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

PPh3 (2.0 eq.) and C2Cl6 (2.0 eq.) were dissolved in DCM (0.72 M) at room temperature and Et3N (4.0 eq.) was added, followed after 5 min of stirring by dropwise addition of a solution of F3 in DCM (0.36 M). The mixture was stirred at room temperature for 1 h and then was diluted with DCM, washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. Crude was purified by column chromatography (eluent: Petroleum ether/EtOAc from 94:6 to 2:3) to give the title compound as orange oil. MS (ES+) C32H37N3O6: 560 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customCrude was purified by column chromatography (eluent: Petroleum ether/EtOAc from 94:6 to 2:3)

Sources & evidence

ORD record
ord-79fa30dd6b064182a1f80ddca50627ad
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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