Ethyl Acetate → (S)-tert-butyl 7-(((benzyloxy)carbonyl)amino)-8-((2-(2-methoxyquinolin-3-yl)-2-oxoethyl)amino)-8-oxooctanoate

HRID 2202558Notes

Reaction equation

HRID 2202558 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)([CH3:4])([CH3:3])[CH3:2].CC[N:19]=C=NCCCN(C)C.Cl.[CH:29]1[CH:30]=[CH:31][C:32]2N(O)N=N[C:33]=2[CH:34]=1.[NH2:39][CH2:40][C:41]([C:43]1[C:44]([O:53][CH3:54])=[N:45][C:46]2[C:51]([CH:52]=1)=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:42].CCN(C(C)C)C(C)C.C[CH2:65][O:66][C:67](C)=[O:68]>CN(C=O)C>[CH2:65]([O:66][C:67]([NH:19][C@H:12]([C:13]([NH:39][CH2:40][C:41]([C:43]1[C:44]([O:53][CH3:54])=[N:45][C:46]2[C:51]([CH:52]=1)=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:42])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[O:68])[C:33]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:34]=1

Participants

8

Reactant 6

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214648798-(tert-Butoxy)-8-oxooctanoic acidHCID 900366552-Amino-1-(2-methoxyquinolin-3-yl)ethan-1-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-2-((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid (prepared as described in WO2006/061638), EDC.HCl (1.3 eq.), HOBt (1.3 eq.) in DMF (0.3 M) was stirred at room temperature for 10 min. Then F2 and DIPEA (3.0 eq.) were added and the resulting mixture was stirred at room temperature for 1 h 30 min. The reaction mixture was diluted with EtOAc, washed with sat. aq. NaHCO3 sol., brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give a crude that was purified by column chromatography (eluent: Petroleum ether/EtOAc from 97:3 to 3:7) to give the title compound as yellow oil. MS (ES+) C32H39N3O7: 578 (M+H)+.

Workup

  1. washwashed with sat. aq. NaHCO3 sol., brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude that
  6. customwas purified by column chromatography (eluent: Petroleum ether/EtOAc from 97:3 to 3:7)

Sources & evidence

ORD record
ord-1fc1af6e869f4578b629186b83b96777
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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