3-(2-Thiazolyl)propionic acid → 3-Thiazol-2-ylpropionic acid (RS)-1-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]ethyl ester

HRID 511049Notes

Reaction equation

HRID 511049 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.[S:37]1[CH:41]=[CH:40][N:39]=[C:38]1[CH2:42][CH2:43][C:44](O)=[O:45]>>[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][C:44](=[O:45])[CH2:43][CH2:42][C:38]5[S:37][CH:41]=[CH:40][N:39]=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 27606093-(2-Thiazolyl)propionic acidHCID 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-one

Product 1

HCID 866705253-Thiazol-2-ylpropionic acid (RS)-1-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl]ethyl esterYield 62%

Procedure

In analogy to Example 5, 150 mg (0.29 mmol) of (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 were converted using 3-(2-thiazolyl)propionic acid and, after workup and purification, 119 mg (62%) of the title compounds were obtained as a colourless foam.

Workup

  1. customafter workup and purification

Sources & evidence

ORD record
ord-1b3ae7bc4b9a4422b2e81aee3b65603d
Source dataset
uspto-grants-2015_08
Patent number
US09096639B2

Reaction notes

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