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 → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butoxycarbonylamino)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

HRID 85620Notes

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.[C:48]([O:52][C:53]([NH:55][CH2:56][CH2:57][NH:58][C@:59]12[CH2:94][CH2:93][C@@H:92]([C:95]([CH3:97])=[CH2:96])[C@@H:60]1[C@@H:61]1[C@@:74]([CH3:77])([CH2:75][CH2:76]2)[C@@:73]2([CH3:78])[C@@H:64]([C@:65]3([CH3:91])[C@@H:70]([CH2:71][CH2:72]2)[C:69]([CH3:80])([CH3:79])[C:68]([C:81]2[CH:90]=[CH:89][C:84]([C:85]([O:87]C)=[O:86])=[CH:83][CH:82]=2)=[CH:67][CH2:66]3)[CH2:63][CH2:62]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>>[C:48]([O:52][C:53]([NH:55][CH2:56][CH2:57][NH:58][C@:59]12[CH2:94][CH2:93][C@@H:92]([C:95]([CH3:97])=[CH2:96])[C@@H:60]1[C@@H:61]1[C@@:74]([CH3:77])([CH2:75][CH2:76]2)[C@@:73]2([CH3:78])[C@@H:64]([C@:65]3([CH3:91])[C@@H:70]([CH2:71][CH2:72]2)[C:69]([CH3:80])([CH3:79])[C:68]([C:81]2[CH:90]=[CH:89][C:84]([C:85]([OH:87])=[O:86])=[CH:83][CH:82]=2)=[CH:67][CH2:66]3)[CH2:63][CH2:62]1)=[O:54])([CH3:49])([CH3:50])[CH3:51]

Participants

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 acid

HCID 86676586methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butoxycarbonylamino)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)benzoate

Product 1

HCID 866765854-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butoxycarbonylamino)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

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-(tert-butoxycarbonylamino)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)benzoate (10 mg, 0.015 mmol) as starting material. The title compound was isolated as a white solid (4 mg, 39%). LCMS: m/e 673.45 (M+H)+, 2.65 min (method 10). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.55 Hz, 2H), 5.51-5.32 (m, 1H), 4.87 (s, 1H), 4.75 (s, 1H), 3.82-3.53 (m, 1H), 3.53-3.24 (m, 3H), 3.04-2.83 (m, 1H), 2.37-1.15 (m, 22H), 1.77 (s, 3H), 1.53-1.49 (m, 9H), 1.27 (s, 3H), 1.14 (s, 3H), 1.11 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Workup

customThe title compound was prepared
customthe hydrolysis method

Sources & evidence

ORD record: ord-b9e53c27b3d144719e1a65c84cbfbc84
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

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