4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-hydroxyethylsulfonyl)ethylamino)-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 → HCID 86676587, compound

HRID 85622Notes

Reaction equation

HRID 85622 reaction equation
OCCS(CCN[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.[NH2:48][CH2:49][CH2:50][NH:51][C@:52]12[CH2:87][CH2:86][C@@H:85]([C:88]([CH3:90])=[CH2:89])[C@@H:53]1[C@@H:54]1[C@@:67]([CH3:70])([CH2:68][CH2:69]2)[C@@:66]2([CH3:71])[C@@H:57]([C@:58]3([CH3:84])[C@@H:63]([CH2:64][CH2:65]2)[C:62]([CH3:73])([CH3:72])[C:61]([C:74]2[CH:83]=[CH:82][C:77]([C:78]([O:80]C)=[O:79])=[CH:76][CH:75]=2)=[CH:60][CH2:59]3)[CH2:56][CH2:55]1>>[NH2:48][CH2:49][CH2:50][NH:51][C@:52]12[CH2:87][CH2:86][C@@H:85]([C:88]([CH3:90])=[CH2:89])[C@@H:53]1[C@@H:54]1[C@@:67]([CH3:70])([CH2:68][CH2:69]2)[C@@:66]2([CH3:71])[C@@H:57]([C@:58]3([CH3:84])[C@@H:63]([CH2:64][CH2:65]2)[C:62]([CH3:73])([CH3:72])[C:61]([C:74]2[CH:75]=[CH:76][C:77]([C:78]([OH:80])=[O:79])=[CH:82][CH:83]=2)=[CH:60][CH2:59]3)[CH2:56][CH2:55]1

Participants

3

Reactant 2

HCID 683579204-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-hydroxyethylsulfonyl)ethylamino)-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 acidHCID 68358226methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-aminoethyl)amino)-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

Product 1

HCID 86676587HCID 86676587, compound

Procedure

The title compound was prepared following the hydrolysis method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-hydroxyethylsulfonyl)ethylamino)-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 using methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-aminoethylamino)-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 (4 mg, 0.006 mmol) as starting material. The title compound was isolated as a white solid (2.4 mg, 67%). LCMS: m/e 573.2 (M+H)+, 2.39 min (method 10). 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=4.27 Hz, 1H), 4.87 (s, 1H), 4.76 (s, 1H), 3.80-3.68 (m, 3H), 3.68-3.59 (m, 1H), 2.97-2.80 (m, 1H), 2.38-1.21 (m, 22H), 1.78 (s, 3H), 1.20 (s, 3H), 1.14 (s, 3H), 1.09 (s, 3H), 1.01 (s, 3H), 1.00 (s, 3H).

Workup

  1. customThe title compound was prepared
  2. customthe hydrolysis method

Sources & evidence

ORD record
ord-7a54f4babb91466d9b0c11d4a1ca75d3
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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