Acetic Acid → HCID 86676406, compound

HRID 405064Notes

Reaction equation

HRID 405064 reaction equation
[CH:1]([C@:3]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:38])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:24])([CH3:23])[C:12]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)=O.C(O)(=O)C.[NH2:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][N:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:54][CH2:53]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C([O-])(O)=O.[Na+]>[C:32]([O:31][C:29]([C:28]1[CH:27]=[CH:26][C:25]([C:12]2[C:13]([CH3:24])([CH3:23])[C@H:14]3[C@:9]([CH3:38])([CH2:10][CH:11]=2)[C@@H:8]2[C@:17]([CH3:22])([C@@:18]4([CH3:21])[C@H:5]([CH2:6][CH2:7]2)[C@H:4]2[C@H:39]([C:42]([CH3:44])=[CH2:43])[CH2:40][CH2:41][C@:3]2([CH2:1][NH:49][CH2:50][CH2:51][N:52]2[CH2:57][CH2:56][N:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:54][CH2:53]2)[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)=[CH:37][CH:36]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86676397HCID 86676397, compound

Product 1

HCID 86676406HCID 86676406, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-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)benzoate (0.1 g, 0.167 mmol) in DCE (2 ml) was added acetic acid (0.019 ml, 0.334 mmol) and 4-N-(2-Aminoethyl)-1-N-Boc-piperazine (0.077 g, 0.334 mmol). The mixture was stirred at rt for 2 h then to the mixture was added sodium triacetoxyborohydride (0.177 g, 0.835 mmol). The mixture was stirred for 3 days at rt then was diluted with 7 ml of sat. NaHCO3 and was extracted with dichloromethane (3×7 ml). The combined organic layers were dried with Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was used in the next step without further purification. LCMS: m/e 812.3 (M+H)+, 3.30 min (method 6).

Workup

  1. stirringThe mixture was stirred for 3 days at rt
  2. extractionwas extracted with dichloromethane (3×7 ml)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude product was used in the next step without further purification
  7. customm/e 812.3 (M+H)+, 3.30 min (method 6)

Sources & evidence

ORD record
ord-d956ff8daff541d48f27d569066004ab
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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