HCID 86731493, compound → (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(2-carboxyethyl)-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

HRID 1773036Notes

Reaction equation

HRID 1773036 reaction equation
C([O:8][C:9]([C@:11]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[CH:16]([C@:17]3([CH3:38])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C:20](/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36])=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)=[O:10])C1C=CC=CC=1.[H][H]>CO.C(OCC)(=O)C.[Pd]>[C:35]([CH2:34][CH2:33][C:20]1[C:21]([CH3:32])([CH3:31])[C@H:22]2[C@:17]([CH3:38])([CH2:18][CH:19]=1)[CH:16]1[C@:25]([CH3:30])([C@@:26]3([CH3:29])[C@H:13]([CH2:14][CH2:15]1)[C@H:12]1[C@H:39]([C:42]([CH3:44])=[CH2:43])[CH2:40][CH2:41][C@:11]1([C:9]([OH:10])=[O:8])[CH2:28][CH2:27]3)[CH2:24][CH2:23]2)([OH:37])=[O:36]

Participants

6

Reactant 2

HCID 86731493HCID 86731493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86731494(1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(2-carboxyethyl)-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 acidYield 9.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E)-3-((1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-3a-(benzyloxycarbonyl)-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)acrylic acid (20 mg, 0.033 mmol) and 10% Pd/C (25 mg, 0.023 mmol) in MeOH (0.5 mL) and ethyl acetate (1 mL) was connected to a balloon of hydrogen and stirred at room temperature for 5 hours. The reaction mixture was filtered to remove Pd/C and the filtrates were concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep HPLC to provide the desired product (1.59 mg, 9%). LCMS: m/e 509.6 (M−H)−, 2.36 min (method 6). 1H NMR (400 MHz, <DMSOmix>) δ 5.21 (d, J=5.0 Hz, 1H), 4.70 (br. s., 1H), 4.57 (br. s., 1H), 3.05-0.98 (m, 27H), 1.67 (s., 3H), 0.96 (s., 6H), 0.93 (s., 3H), 0.89 (s., 3H), 0.79 (s., 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove Pd/C
  3. concentrationthe filtrates were concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DMF
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-3b647cfe891d4c549136b9c63c8f1abc
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

Loading…