Thionyl Chloride → HCID 56846882, compound

HRID 1473876Notes

Reaction equation

HRID 1473876 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10](=[O:39])[O:11][C@@H:12]2[CH2:28][C@@H:27]3[C@@:15]([CH3:38])([C@@H:16]4[C@@H:24]([CH2:25][CH2:26]3)[C@:23]3(O)[C@@:19]([CH3:37])([C@@H:20]([C:30]5[CH:31]=[CH:32][C:33](=[O:36])[O:34][CH:35]=5)[CH2:21][CH2:22]3)[CH2:18][CH2:17]4)[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.O=S(Cl)Cl>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10](=[O:39])[O:11][C@@H:12]2[CH2:28][C@@H:27]3[C@@:15]([CH3:38])([C@@H:16]4[C@@H:24]([CH2:25][CH2:26]3)[C:23]3[C@@:19]([CH3:37])([C@@H:20]([C:30]5[CH:31]=[CH:32][C:33](=[O:36])[O:34][CH:35]=5)[CH2:21][CH:22]=3)[CH2:18][CH2:17]4)[CH2:14][CH2:13]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53308214HCID 53308214, compound

Product 1

HCID 56846882HCID 56846882, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-morpholinoethylcarbamate (43.7 mg, 0.08 mmol, 1 eq) in pyridine (3 mL) was added SOCl2 (57.1 mg, 0.48 mmol) at 0° C. The mixture was stirred at this temperature for about 2 h, quenched with saturated NaHCO3, and extracted with EtOAc. The organic layers were combined, dried with Na2SO4, concentrated and purified via Preparative TLC to afford (3S,5R,8R,9S,10S,13R,17S)-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-morpholinoethylcarbamate (20 mg, 47.6%). LCMS (M+H+) m/z calculated 524.33. found 526.0. 1H NMR (CD3OD, 400 MHz) δ 7.64 (m, 2 H), 6.38 (m, 1 H), 5.37 (m, 1 H), 4.98 (m, 1 H), 3.78 (m, 4 H), 3.34 (m, 2H), 2.92 (m, 1 H), 2.90 (m, 7H), 2.50-1.30 (m, 18 H), 1.10(s, 3 H), 0.83 (s, 3 H).

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified via Preparative TLC

Sources & evidence

ORD record
ord-d2ceffcac398405d91caba371208160e
Source dataset
uspto-grants-2015_04
Patent number
US09018197B2

Reaction notes

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