Boronic Acid → HCID 54759390, compound

HRID 406879Notes

Reaction equation

HRID 406879 reaction equation
C(CCC1C=CC([C:12]2[C:13]([CH3:43])([CH3:42])[C@H:14]3[C@:27]([CH3:30])([CH2:28][CH:29]=2)[C@@H:26]2[C@:17]([CH3:41])([C@@:18]4([CH3:40])[C@H:23]([CH2:24][CH2:25]2)[C@H:22]2[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]2([C:37]([OH:39])=[O:38])[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)=CC=1)(O)=O.B([C:47]1[CH:55]=[CH:54][C:50]([C:51]([OH:53])=[O:52])=[C:49]([Cl:56])[CH:48]=1)(O)O.B(O)O>>[C:51]([C:50]1[CH:54]=[CH:55][C:47]([C:12]2[C:13]([CH3:43])([CH3:42])[C@H:14]3[C@:27]([CH3:30])([CH2:28][CH:29]=2)[C@@H:26]2[C@:17]([CH3:41])([C@@:18]4([CH3:40])[C@H:23]([CH2:24][CH2:25]2)[C@H:22]2[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]2([C:37]([OH:39])=[O:38])[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)=[CH:48][C:49]=1[Cl:56])([OH:53])=[O:52]

Participants

4

Reactant 3

HCID 61668Boronic AcidHCID 149032234-Borono-2-chlorobenzoic acidHCID 54761941(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-[4-(2-carboxyethyl)phenyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Product 1

HCID 54759390HCID 54759390, compound

Procedure

The title compound was prepared following the method described above for compound (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(2-carboxyethyl)phenyl)-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]chrysene-3a-carboxylic acid (example 4a) using 4-borono-2-chlorobenzoic acid as the reactant boronic acid. Purification of the product was accomplished by first using Biotage flash chromatography with a 0-50% ethyl acetate in hexanes gradient with 0.1% acetic acid added to the mixture. The compound was not sufficiently pure, so further purification by prep HPLC followed (acetonitrile/water mobile phase with TFA buffer on a C18 reverse phase column). After concentrating the desired fractions, the title compound was isolated as a white film (6.1 mg, 6.8% yield over two steps). LCMS: m/e 591.60 (M−H)−, 1.54 min (method 1). 1H NMR (500 MHz, Pyr) δ ppm 0.92 (br. s., 6H), 0.96 (s, 3H), 1.10 (s, 3H), 1.11 (s, 3H), 1.18-1.84 (m, 15H), 1.83 (s, 3H), 1.89 (t, J=13.28 Hz, 1H), 1.99 (br. s., 1H), 2.09 (dd, J=17.09, 6.10 Hz, 1H), 2.24-2.33 (m, 2H), 2.66 (d, J=12.51 Hz, 1H), 2.81 (t, J=11.75 Hz, 1H), 3.54-3.63 (m, 1H), 4.82 (s, 1H), 5.00 (s, 1H), 5.37 (d, J=5.80 Hz, 1H), 7.24 (d, J=8.24 Hz, 1H), 7.51 (s, 1H), 8.21 (d, J=7.63 Hz, 1H).

Workup

  1. customThe title compound was prepared
  2. customPurification of the product
  3. additionadded to the mixture
  4. customso further purification by prep HPLC
  5. concentrationAfter concentrating the desired fractions

Sources & evidence

ORD record
ord-e6515c4dbd95454b8c51c65276ea1e76
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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