Ethyl Acetate → HCID 58840906, compound

HRID 1715069Notes

Reaction equation

HRID 1715069 reaction equation
C(O[C:6](=[O:27])[C@@H:7]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(C)(C)C.[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2.CCN=C=N[CH2:44][CH2:45][CH2:46]N(C)C.[C:50](OCC)(=O)C>CC#N>[C:45]([O:15][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C:6](=[O:27])[NH:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)([CH3:46])([CH3:50])[CH3:44]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 113736-AminoquinolineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68637473HCID 68637473, compound

Product 1

HCID 58840906HCID 58840906, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(7S)-7-Benzyloxycarbonylamino-octanedioic acid 8-tert-butyl ester (10.0 g, 26.3 mmol), 6-aminoquinoline (4.02 g, 27.9 mmol) and EDCI (6.07 g, 29.0 mmol) were dissolved in 150 mL anhydrous CH3CN. The solution was stirred at RT for 2 h. The solvent was removed under reduced pressure, and the residue was dissolved in 500 mL EtOAc and washed with 1 M HCl (200×3) and water (100×2). The organic layer was dried over anhydrous Na2SO4 Removal of solvent gave 16 g crude product. The pure compound 9.0 g was obtained with column separation (ethyl acetate as eluent) in 68% as a thick oil. 1H NMR (CDCl3) δ 8.80 (1H, d), 8.70 (1H, s), 8.30 (1H, d), 8.00 (2H, t), 7.56-7.20 (7H), 5.40 (1H, d), 5.08 (2H, s), 4.38 (1H, m), 2.20 (2H, t), 2.0-1.6 (17H, m).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 500 mL EtOAc
  3. washwashed with 1 M HCl (200×3) and water (100×2)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4 Removal of solvent
  5. customgave 16 g crude product

Sources & evidence

ORD record
ord-a80a72affb284ca4b6ace57bc8b8e4c6
Source dataset
uspto-grants-2010_09
Patent number
US07799803B2

Reaction notes

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