Ethyl Acetate → HCID 86673526, compound

HRID 1424557Notes

Reaction equation

HRID 1424557 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:4]([NH:6][C@H:7]([C:13]([OH:15])=O)[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:5])[CH3:3].C1C=C[C:26]2N(O)N=N[C:27]=2[CH:28]=1.[CH2:33]1CCC(N=C=NC2CCCCC2)CC1.[F:48][C:49]1[C:54]([F:55])=[C:53]([C:56]#[C:57][C:58]2[CH:64]=[CH:63][C:61]([NH2:62])=[CH:60][CH:59]=2)[C:52]([F:65])=[C:51]([F:66])[N:50]=1.C([O:69][C:70](=[O:72])C)C>C(Cl)Cl>[C:27]([O:72][C:70](=[O:69])[NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([NH:6][C:4](=[O:5])[CH:2]([NH:1][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:3])[C:13](=[O:15])[NH:62][C:61]1[CH:63]=[CH:64][C:58]([C:57]#[C:56][C:53]2[C:52]([F:65])=[C:51]([F:66])[N:50]=[C:49]([F:48])[C:54]=2[F:55])=[CH:59][CH:60]=1)([CH3:26])([CH3:28])[CH3:33]

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 20112045N-(tert-Butoxycarbonyl)-L-alanyl-L-lysineHCID 68578502HCID 68578502, compound

Product 1

HCID 86673526HCID 86673526, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acid Boc-Ala-Lys-OH, (21) (207 mg, 0.5 mmol) in CH2Cl2 (5 mL) at 0° C., was sequentially treated with HOBt (101 mg, 0.75 mmol) and DCC (154 mg, 0.75 mmol). After 15 min., 4-((perfluoropyridin-4-yl)ethynyl)aniline (7) (154 mg, 0.08 mmol) was added to the reaction mixture. After stirring for 1 days at room temperature, the reaction mixture was diluted with ethylacetate, washed with saturated NH4Cl solution, saturated NaHCO3, 1 N HCl, water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Chromatographic purification (SiO2, 50% ethylacetate in hexane) of the residue provided (22) (170 mg, 52%) as a white solid; 1H NMR (400 MHz, CD3OD): 1H NMR (400 MHz, CDCl3): δ 9.17 (bs, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 6.91 (bs, 1H), 5.22 (bs, 1H) , 4.75 (bs, 1H) , 4.57 (bs, 1H) , 4.21-4.12 (m, 1H), 3.17-3.05 (m, 2H), 1.81-1.62 (m, 2H), 1.61-1.31 (m, 25H); MS (ESI): m/z (%) 688 (100) [M+Na]+;

Workup

  1. washwashed with saturated NH4Cl solution, saturated NaHCO3, 1 N HCl, water, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customChromatographic purification (SiO2, 50% ethylacetate in hexane) of the residue

Sources & evidence

ORD record
ord-a781283e89b24e4f873e80084ff41b3a
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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