1,2-Dichloroethane → (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-((4-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoyl)oxy)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acid

HRID 524455Notes

Reaction equation

HRID 524455 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]([CH3:13])([CH3:12])[CH2:8][C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.O[C@H:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:22]([CH2:23][CH2:24][C@:25]3([CH3:52])[C@@H:34]2[CH2:33][CH2:32][C@H:31]2[C@@:26]3([CH3:51])[CH2:27][CH2:28][C@@:29]3(/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49])[CH2:41][C:40](=[O:42])[C:39]([CH:43]([CH3:45])[CH3:44])=[C:30]32)[C:21]1([CH3:54])[CH3:53]>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6](=[O:14])[C:7]([CH3:13])([CH3:12])[CH2:8][C:9]([O:11][C@H:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:22]([CH2:23][CH2:24][C@:25]3([CH3:52])[C@@H:34]2[CH2:33][CH2:32][C@H:31]2[C@@:26]3([CH3:51])[CH2:27][CH2:28][C@@:29]3(/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49])[CH2:41][C:40](=[O:42])[C:39]([CH:43]([CH3:45])[CH3:44])=[C:30]32)[C:21]1([CH3:53])[CH3:54])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 235551774-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoic acidHCID 89661781(E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acid

Product 1

HCID 117701488(E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-((4-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoyl)oxy)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acidYield 80.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(tert-butoxy)-3,3-dimethyl-4-oxobutanoic acid (122 mg, 0.604 mmol), DMAP (123 mg, 1.007 mmol) and EDC (193 mg, 1.007 mmol) in dichloromethane (12 mL) stirred at room temp for 30 min was added (E)-3-((3aS,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-3a-yl)acrylic acid (100 mg, 0.201 mmol). The reaction mixture was stirred at 25° C. for 3 h. The produce was extracted with DCM (15 mL*3), the combined organic phase was washed with brine (20 mL), dried, and the solvent removed under reduced pressure to give 110 mg of residue as light yellow solid which was used in the next reaction without further purification.

Workup

  1. extractionThe produce was extracted with DCM (15 mL*3)
  2. washthe combined organic phase was washed with brine (20 mL)
  3. customdried
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6f54646f22aa4748835f7d898d9df4af
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

Loading…