Iodoethane → HCID 67775911, compound

HRID 2405506Notes

Reaction equation

HRID 2405506 reaction equation
[C:1]([CH2:4]CN(CC)CCNC([C@]12CC[C@@H](C(C)=C)[C@@H]1[C@@H]1[C@@](C)(CC2)[C@@]2(C)[C@@H]([C@]3(C)[C@@H](CC2)C(C)(C)C(C2C=CC(C(O)=O)=CC=2)=CC3)CC1)=O)(O)=O.C[O:53][C:54](=[O:103])[CH2:55][CH2:56][NH:57][CH2:58][CH2:59][CH2:60][NH:61][C:62]([C@:64]12[CH2:99][CH2:98][C@@H:97]([C:100]([CH3:102])=[CH2:101])[C@@H:65]1[C@@H:66]1[C@@:79]([CH3:82])([CH2:80][CH2:81]2)[C@@:78]2([CH3:83])[C@@H:69]([C@:70]3([CH3:96])[C@@H:75]([CH2:76][CH2:77]2)[C:74]([CH3:85])([CH3:84])[C:73]([C:86]2[CH:95]=[CH:94][C:89]([C:90]([O:92]C)=[O:91])=[CH:88][CH:87]=2)=[CH:72][CH2:71]3)[CH2:68][CH2:67]1)=[O:63].ICC>>[C:54]([CH2:55][CH2:56][N:57]([CH2:1][CH3:4])[CH2:58][CH2:59][CH2:60][NH:61][C:62]([C@:64]12[CH2:99][CH2:98][C@@H:97]([C:100]([CH3:102])=[CH2:101])[C@@H:65]1[C@@H:66]1[C@@:79]([CH3:82])([CH2:80][CH2:81]2)[C@@:78]2([CH3:83])[C@@H:69]([C@:70]3([CH3:96])[C@@H:75]([CH2:76][CH2:77]2)[C:74]([CH3:85])([CH3:84])[C:73]([C:86]2[CH:87]=[CH:88][C:89]([C:90]([OH:92])=[O:91])=[CH:94][CH:95]=2)=[CH:72][CH2:71]3)[CH2:68][CH2:67]1)=[O:63])([OH:53])=[O:103]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 54764882HCID 54764882, compoundHCID 67775121HCID 67775121, compound

Product 1

HCID 67775911HCID 67775911, compound

Procedure

The title compound was prepared following the method described above for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-((2-carboxyethyl)(ethyl)amino)ethylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid (example 89) using methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(3-methoxy-3-oxopropylamino)propylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate as amine and iodoethane as alkylating reagent. The product was isolated as a white solid (3 mg, 30%). LCMS: m/e 715.49 (M+H)+, 2.11 min (method 1). 1H NMR (500 MHz, Acetic Acid-d4) δ ppm 8.03 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.37 (d, J=5.19 Hz, 1H), 4.78 (s, 1H), 4.65 (s, 1H), 3.50 (t, J=7.17 Hz, 2H), 3.46-3.40 (m, 2H), 3.39-3.31 (m, 2H), 3.27 (t, J=7.63 Hz, 2H), 3.21-3.08 (m, 1H), 2.97 (t, J=7.02 Hz, 2H), 2.67-2.54 (m, 1H), 2.25-2.17 (m, 2H), 1.74 (s, 3H), 1.39 (t, J=7.17 Hz, 3H), 2.05-1.10 (m, 21H), 1.08 (s, 3H), 1.06 (s, 6H), 1.01 (s, 3H), 0.99 (s, 3H).

Sources & evidence

ORD record
ord-2778aff3bd0844ffb0d355e0d1b19b97
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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