Water → 1-tert-Butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((S)-1-(3-chlorophenyl)ethyl)amino)-3-oxoprop-1-en-1-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 524479Notes

Reaction equation

HRID 524479 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].CCN=C=NCCCN(C)C.Cl.[Cl:27][C:28]1[CH:29]=[C:30]([C@@H:34]([NH:36][C:37](=[O:70])/[CH:38]=[CH:39]/[C@:40]23[CH2:66][CH2:65][C:64]([CH:67]([CH3:69])[CH3:68])=[C:41]2[C@@H:42]2[C@@:55]([CH3:58])([CH2:56][CH2:57]3)[C@@:54]3([CH3:59])[C@@H:45]([C@:46]4([CH3:63])[C@@H:51]([CH2:52][CH2:53]3)[C:50]([CH3:61])([CH3:60])[C@@H:49](O)[CH2:48][CH2:47]4)[CH2:44][CH2:43]2)[CH3:35])[CH:31]=[CH:32][CH:33]=1.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:12][C:7]([CH3:13])([CH2:8][C:9]([O:11][C@H:49]1[CH2:48][CH2:47][C@@:46]2([CH3:63])[C@@H:51]([CH2:52][CH2:53][C@:54]3([CH3:59])[C@@H:45]2[CH2:44][CH2:43][C@H:42]2[C@@:55]3([CH3:58])[CH2:56][CH2:57][C@@:40]3(/[CH:39]=[CH:38]/[C:37]([NH:36][C@H:34]([C:30]4[CH:31]=[CH:32][CH:33]=[C:28]([Cl:27])[CH:29]=4)[CH3:35])=[O:70])[CH2:66][CH2:65][C:64]([CH:67]([CH3:69])[CH3:68])=[C:41]32)[C:50]1([CH3:60])[CH3:61])=[O:10])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235551774-(Tert-butoxy)-3,3-dimethyl-4-oxobutanoic acidHCID 117701506(E)-N-((S)-1-(3-Chlorophenyl)ethyl)-3-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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)acrylamide

Product 1

HCID 1177015001-tert-Butyl 4-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((E)-3-(((S)-1-(3-chlorophenyl)ethyl)amino)-3-oxoprop-1-en-1-yl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-tert-butoxy-3,3-dimethyl-4-oxobutanoic acid (1.174 g, 5.80 mmol), DMAP (0.709 g, 5.80 mmol) in DCM (20 mL) stirred at rt was added EDCl (1.854 g, 9.67 mmol). The reaction mixture was stirred at rt for 2 h. (E)-N—((S)-1-(3-Chlorophenyl)ethyl)-3-((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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)acrylamide (1.2 g, 1.934 mmol) was added to the reaction mixture. The resultant mixture was stirred at rt overnight. Water was added and the mixture was partitioned and washed with additional water. The organics were dried over sodium sulfate filtered through a short silica gel column and evaporated in vacuo to give the crude product as yellow foam. This material was used in the next step without further purification.

Workup

  1. additionwas added to the reaction mixture
  2. customthe mixture was partitioned
  3. washwashed with additional water
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered through a short silica gel column
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d89f770c8d204233996dcaf33f825f44
Source dataset
uspto-grants-2016_05
Patent number
US09340513B2

Reaction notes

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