HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzoyl chloride → 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-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-9-yl) 2,2-dimethylsuccinate

HRID 513903
Notes
Print preview

Reaction equation

HRID 513903 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([CH:28]=[O:29])[CH2:23][C:22](=[O:24])[C:21]([CH:25]([CH3:27])[CH3:26])=[C:12]32)[C:3]1([CH3:33])[CH3:32].[C:34]([O:38][C:39](=[O:47])[C:40]([CH3:46])([CH3:45])[CH2:41][C:42](O)=[O:43])([CH3:37])([CH3:36])[CH3:35].C(Cl)(=O)C1C=CC=CC=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O.C(OCC)(=O)C.C1COCC1>[CH3:45][C:40]([CH3:46])([CH2:41][C:42]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([CH:28]=[O:29])[CH2:23][C:22](=[O:24])[C:21]([CH:25]([CH3:27])[CH3:26])=[C:12]32)[C:3]1([CH3:32])[CH3:33])=[O:43])[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 235551774-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoic acidHCID 86690401(3aR,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]chrysene-3a-carbaldehyde

Product 1

HCID 86690400
1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-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-9-yl) 2,2-dimethylsuccinate

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3aR,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]chrysene-3a-carbaldehyde (26.9 g, 1 equiv), 4-(tert-butoxy)-3,3-dimethyl-4-oxobutanoic acid (14.96 g, 1.25 equiv) and THF (538 ml, 20 vol) were charged to a flask. Benzoyl chloride (10.4 g, 1.25 equiv) was added followed by slow addition of triethylamine (14.97 g, 2.5 equiv) forming a thick slurry. DMAP (0.1.81 g, 0.25 equiv) was added and the reaction was allowed to stir at ambient temperature for approximately 18 hours until complete by HPLC. Reaction was then charged with ethyl acetate (538 mL, 20 vol) and water (269 ml, 10 vol), stirred well and allowed to settle. Aqueous phase was removed and the organic phase washed with saturated sodium bicarbonate solution (2×10 vol) followed by water (269 mL, 10 vol). The reaction solution evaporated under vacuum to approximately 4 volumes to produce solids. Additional hexanes (269 ml, 10 vol) was added and reaction heated back to reflux to nearly form solution and slowly cooled to ambient temperature (seeding with desired product) and let stir for 15 minutes then cooled to 0° C. for approximately two hours and filtered solid. Washed solid with hexanes (2×10 vol) and dried at 50° C. under vacuum to a weight of 32.15 g, 85% yield of 1-tert-butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-formyl-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-9-yl) 2,2-dimethylsuccinate.

Workup

  1. customforming a thick slurry
  2. customReaction
  3. stirringstirred well
  4. customAqueous phase was removed
  5. washthe organic phase washed with saturated sodium bicarbonate solution (2×10 vol)
  6. customThe reaction solution evaporated under vacuum to approximately 4 volumes
  7. customto produce solids
  8. customreaction
  9. temperatureheated back
  10. temperatureto reflux
  11. customto nearly form solution

Sources & evidence

ORD record
ord-1e9fd932e27242738b3f0409af9286ab
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102685B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes