Lawesson's reagent → HCID 86741438, compound

HRID 543013Notes

Reaction equation

HRID 543013 reaction equation
COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[CH2:23]([NH:27][C:28](=O)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C@@H:39]1[CH2:56][C:55]2[CH:54]=[C:53]([O:57][CH3:58])[CH:52]=[CH:51][C:50]=2[C@@H:49]2[C@@H:40]1[C@H:41]1[C@@:45]([CH2:47][CH2:48]2)([CH3:46])[C@@H:44]([O:59]C2CCCCO2)[CH2:43][CH2:42]1)[CH2:24][CH2:25][CH3:26]>C1(C)C(C)=CC=CC=1>[CH2:23]([NH:27][C:28](=[S:10])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C@@H:39]1[CH2:56][C:55]2[CH:54]=[C:53]([O:57][CH3:58])[CH:52]=[CH:51][C:50]=2[C@@H:49]2[C@@H:40]1[C@H:41]1[C@@:45]([CH2:47][CH2:48]2)([CH3:46])[C@@H:44]([OH:59])[CH2:43][CH2:42]1)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86741439HCID 86741439, compound

Product 1

HCID 86741438HCID 86741438, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

2,4-Bis-(p-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's Reagent; 0.375 g.) was added to a stirred solution of N-n-butyl-11-(3-methoxy-17β-tetrahydropyranyloxyoestra-1,3,5(10)-trien-7α-yl)undecanamide (0.25 g.) in xylene (14 ml.) and the mixture was stirred and heated at 130° C. for 5 hours and then evaporated to dryness under reduced pressure. The residue was dissolved in a mixture of tetrahydrofuran (2 ml.), water (2 ml.) and acetic acid (4 ml.) and the solution was stirred at laboratory temperature for 16 hours and then evaporated to dryness under reduced pressure. The residue was purified by chromatography on a silica gel column using a 4:1 v/v mixture of toluene and ethyl acetate as eluant, and there was thus obtained as an oil N-n-butyl-11-(17β-hydroxy-3-methoxyoestra-1,3,5(10)-trien-7α-yl)thioundecanamide.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of tetrahydrofuran (2 ml.), water (2 ml.) and acetic acid (4 ml.)
  3. stirringthe solution was stirred at laboratory temperature for 16 hours
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. additiona 4:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-b4a7692bdd1c41439306f31521eb1f67
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

Loading…