1,2-Dichloroethane → HCID 86692353, compound

HRID 1400996Notes

Reaction equation

HRID 1400996 reaction equation
[O:1]=[S:2]1(=[O:49])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][C@:11]23[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:42])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]3[CH2:38][CH2:37][CH:36]([C:39](O)=[O:40])[CH2:35][CH:34]=3)=[CH:19][CH2:18]4)[CH2:15][CH2:14]2)[CH2:4][CH2:3]1.S(Cl)([Cl:52])=O.ClCCCl.C1COCC1>ClCCl.CO>[O:1]=[S:2]1(=[O:49])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][C@:11]23[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:42])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]3[CH2:38][CH2:37][CH:36]([C:39]([Cl:52])=[O:40])[CH2:35][CH:34]=3)=[CH:19][CH2:18]4)[CH2:15][CH2:14]2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 86575409HCID 86575409, compound

Product 1

HCID 86692353HCID 86692353, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-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)cyclohex-3-enecarboxylic acid (0.1 g, 0.144 mmol) in dichloromethane (4 mL) was added thionyl chloride (0.105 mL, 1.439 mmol). The mixture was attached to a reflux condensor and was heated to reflux. The solids did not completely dissolve, so DCE (3 mL) was added and the mixture was warmed to 60° C. with a reflux condensor attached. Solids still remained, so THF (2 mL) was added and the mixture was further heated to 70° C. The solids never completely dissolved, but the reaction was allowed to reflux regardless. After 4 h of heating, the mixture was cooled to rt. LC/MS showed the methyl ester since methanol was added to analytical sample to help solubilize the product for analysis. The mixture was concentrated under reduced pressure, then was diluted with dichloromethane and concentrated two additional times. The crude product was used in the next step with no additional purification. LCMS: m/e 709.7 (M+MeOH)+, 2.08 min (method 1).

Workup

  1. temperaturewas heated to reflux
  2. dissolutionThe solids did not completely dissolve
  3. temperaturethe mixture was further heated to 70° C
  4. dissolutionThe solids never completely dissolved
  5. temperatureto reflux regardless
  6. temperatureAfter 4 h of heating
  7. temperaturethe mixture was cooled to rt
  8. additionwas added to analytical sample
  9. concentrationThe mixture was concentrated under reduced pressure
  10. additionwas diluted with dichloromethane
  11. concentrationconcentrated two additional times
  12. customThe crude product was used in the next step with no additional purification
  13. customm/e 709.7 (M+MeOH)+, 2.08 min (method 1)

Sources & evidence

ORD record
ord-72cfd9dcce9345b9851ddd1b439831fa
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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