Thionyl Chloride → HCID 56846769, compound

HRID 1473875Notes

Reaction equation

HRID 1473875 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9](=[O:38])[O:10][C@@H:11]2[CH2:27][C@@H:26]3[C@@:14]([CH3:37])([C@@H:15]4[C@@H:23]([CH2:24][CH2:25]3)[C@:22]3(O)[C@@:18]([CH3:36])([C@@H:19]([C:29]5[CH:30]=[CH:31][C:32](=[O:35])[O:33][CH:34]=5)[CH2:20][CH2:21]3)[CH2:17][CH2:16]4)[CH2:13][CH2:12]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)Cl>N1C=CC=CC=1>[N:1]1([CH2:6][CH2:7][NH:8][C:9](=[O:38])[O:10][C@@H:11]2[CH2:27][C@@H:26]3[C@@:14]([CH3:37])([C@@H:15]4[C@@H:23]([CH2:24][CH2:25]3)[C:22]3[C@@:18]([CH3:36])([C@@H:19]([C:29]5[CH:30]=[CH:31][C:32](=[O:35])[O:33][CH:34]=5)[CH2:20][CH:21]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53308212HCID 53308212, compound

Product 1

HCID 56846769HCID 56846769, compoundYield 78.7%

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-(pyrrolidin-1-yl)ethylcarbamate (54 mg, 0.1 mmol, 1 eq) in pyridine (3 mL) was added SOCl2(71.4 mg, 0.6 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-(pyrrolidin-1-yl)ethylcarbamate (40 mg, 78.7%). LCMS (M+H+) m/z calculated 508.33. found 509.4. 1H NMR (CD3OD, 400 MHz) δ 7.63 (m, 2 H), 6.38 (m, 1 H), 5.36 (m, 1 H), 5.00 (m, 1 H), 3.38 (m, 2 H), 3.10 (m, 6 H), 2.90 (m, 1H), 2.60 (m, 1 H), 2.50 (m, 1 H), 2.30-1.30 (m, 21 H), 1.10(s, 3 H), 0.86 (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-be4fbca86d154f3882c6a18a0677cf96
Source dataset
uspto-grants-2015_04
Patent number
US09018197B2

Reaction notes

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