(8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-1 3-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one → (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-{4-[(RS)-1-(2-methylbenzothiazol-5-ylmethoxy)ethyl]phenyl}-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

HRID 511040Notes

Reaction equation

HRID 511040 reaction equation
[OH:1][C@:2]1([C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[C@:18]2([CH3:19])[C@H:5]([C@H:6]3[C:15]([C@@H:16]([C:20]4[CH:25]=[CH:24][C:23]([CH:26]([OH:28])[CH3:27])=[CH:22][CH:21]=4)[CH2:17]2)=[C:14]2[C:9](=[CH:10][C:11](=[O:29])[CH2:12][CH2:13]2)[CH2:8][CH2:7]3)[CH2:4][CH2:3]1.Br[CH2:38][C:39]1[CH:40]=[CH:41][C:42]2[S:46][C:45]([CH3:47])=[N:44][C:43]=2[CH:48]=1>>[OH:1][C@:2]1([C:30]([F:35])([F:36])[C:31]([F:32])([F:33])[F:34])[C@:18]2([CH3:19])[C@H:5]([C@H:6]3[C:15]([C@@H:16]([C:20]4[CH:21]=[CH:22][C:23]([CH:26]([O:28][CH2:38][C:39]5[CH:40]=[CH:41][C:42]6[S:46][C:45]([CH3:47])=[N:44][C:43]=6[CH:48]=5)[CH3:27])=[CH:24][CH:25]=4)[CH2:17]2)=[C:14]2[C:9](=[CH:10][C:11](=[O:29])[CH2:12][CH2:13]2)[CH2:8][CH2:7]3)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 18346565(8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-1 3-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-oneHCID 211907575-Bromomethyl-2-methylbenzothiazole

Product 1

HCID 50915135(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-{4-[(RS)-1-(2-methylbenzothiazol-5-ylmethoxy)ethyl]phenyl}-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-oneYield 24%

Procedure

In analogy to Example 2, 500 mg (0.98 mmol) of (8S,11R,13S,14S,17S)-17-hydroxy-11-[4-((RS)-1-hydroxyethyl)phenyl]-13-methyl-17-pentafluoroethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one were converted using 5-bromomethyl-2-methylbenzothiazole and, after workup and purification, 157 mg (24%) of the title compound were isolated as a colourless foam.

Workup

  1. customafter workup and purification

Sources & evidence

ORD record
ord-1be6cf4b0df04b098f35f9bb8a072eea
Source dataset
uspto-grants-2015_08
Patent number
US09096640B2

Reaction notes

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