Chloride → HCID 50923525, compound

HRID 2179805Notes

Reaction equation

HRID 2179805 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:34])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:33])[CH2:12][CH2:13][C@@:14]3([C:30](O)=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:36])[CH3:35])(=[O:3])[CH3:2].[Cl-].[CH3:38][CH:39]1[CH2:44][CH2:43][CH2:42][N:41]([CH2:45][C@H:46]2[CH2:50][CH2:49][C@@H:48]([NH2:51])[CH2:47]2)[CH2:40]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:34])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:33])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:31])[NH:51][C@@H:48]4[CH2:49][CH2:50][C@H:46]([CH2:45][N:41]5[CH2:42][CH2:43][CH2:44][CH:39]([CH3:38])[CH2:40]5)[CH2:47]4)[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:36])[CH3:35])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 312ChlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 1030053410376-50-8HCID 66861077HCID 66861077, compound2×

Product 1

HCID 50923525HCID 50923525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (0.5 g, 1.04 mmol) (Prepared as described in J. Med. Chem. 2009. 52, 3248-3258) in 50 ml DCM, Oxallyl chloride (2 ml, 15.87 mmol) was added and stirred at room temperature for about 6 hours. Completion of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue was taken in DCM (15 ml) then kept under N2 atmosphere. (1R,3S)-3-((3-methylpiperidin-1-yl)methyl)cyclopentanamine (Intermediate 10, 0.21 g) in DCM, triethyl amine (0.3 ml, 3.12 mmol) was added at 0° C. and stirred for about 15 minutes followed by above prepared acid chloride was added and stirred at room temperature for about 8 hours. Completion of the reaction was monitored by TLC. The reaction mixture was neutralized with sat. NaHCO3 and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 50% ethyl acetate in hexane as eluent to furnish the title compound as a white solid. 1H NMR (300 MHz, CDCl3): 0.57-0.97 (m, 19H); 1.18-1.21 (m, 8H); 1.25-1.41 (m, 12H); 1.49-1.62 (m, 8H); 1.65-1.82 (m, 10H); 1.85-1.98 (m, 4H); 2.56-2.69 (m, 2H); 2.88-3.06 (m, 3H); 3.29-3.38 (m, 1H); 3.89-3.90 (m, 1H); 4.25-4.70 (m, 4H); 5.78 (s, 1H); 6.12-6.15 (m, 1H); MASS: 763 (100%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringstirred for about 15 minutes
  3. additionwas added
  4. stirringstirred at room temperature for about 8 hours
  5. extractionextracted with DCM
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1504abcdcba5462d8e470f43827d6bfc
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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