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 86676588, compound

HRID 85625Notes

Reaction equation

HRID 85625 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][CH2:58][NH:59][C@:60]12[CH2:95][CH2:94][C@@H:93]([C:96]([CH3:98])=[CH2:97])[C@@H:61]1[C@@H:62]1[C@@:75]([CH3:78])([CH2:76][CH2:77]2)[C@@:74]2([CH3:79])[C@@H:65]([C@:66]3([CH3:92])[C@@H:71]([CH2:72][CH2:73]2)[C:70]([CH3:81])([CH3:80])[C:69]([C:82]2[CH:91]=[CH:90][C:85]([C:86]([O:88]C)=[O:87])=[CH:84][CH:83]=2)=[CH:68][CH2:67]3)[CH2:64][CH2:63]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>>[C:48]([O:52][C:53]([NH:55][CH2:56][CH2:57][CH2:58][NH:59][C@:60]12[CH2:95][CH2:94][C@@H:93]([C:96]([CH3:98])=[CH2:97])[C@@H:61]1[C@@H:62]1[C@@:75]([CH3:78])([CH2:76][CH2:77]2)[C@@:74]2([CH3:79])[C@@H:65]([C@:66]3([CH3:92])[C@@H:71]([CH2:72][CH2:73]2)[C:70]([CH3:81])([CH3:80])[C:69]([C:82]2[CH:83]=[CH:84][C:85]([C:86]([OH:88])=[O:87])=[CH:90][CH:91]=2)=[CH:68][CH2:67]3)[CH2:64][CH2:63]1)=[O:54])([CH3:49])([CH3:50])[CH3:51]

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 86676589methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(tert-butoxycarbonylamino)propylamino)-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 86676588HCID 86676588, 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-(3-(tert-butoxycarbonylamino)propylamino)-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 (5 mg, 0.007 mmol) as starting material. The title compound was isolated as a white solid (3 mg, 58%). LCMS: m/e 687.54 (M+H)+, 2.69 min (method 10). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.37 (d, J=4.58 Hz, 1H), 4.87 (s, 1H), 4.74 (s, 1H), 3.38-3.17 (m, 4H), 3.04-2.86 (m, 1H), 2.36-1.17 (m, 24H), 1.77 (s, 3H), 1.50 (s, 9H), 1.25 (s, 3H), 1.14 (s, 3H), 1.09 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-a4d745cc16f74df381c259999f4e2c5f
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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