Water → (S)-2-tert-Butoxycarbonylamino-3-methylbutyric 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 511043Notes

Reaction equation

HRID 511043 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.[C:37]([O:41][C:42]([NH:44][C@@H:45]([CH:49]([CH3:51])[CH3:50])[C:46](O)=[O:47])=[O:43])([CH3:40])([CH3:39])[CH3:38].Cl.CN(C)CCCN=C=NCC.O>N1C=CC=CC=1.CN(C)C1C=CN=CC=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][C:46](=[O:47])[C@@H:45]([NH:44][C:42]([O:41][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:43])[CH:49]([CH3:51])[CH3:50])[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

7

Reactant 4

HCID 962WaterHCID 83693Boc-L-ValineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 86670518(S)-2-tert-Butoxycarbonylamino-3-methylbutyric 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 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
23 °C

Procedure

The solution of 300 mg (0.59 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 in 3 ml of pyridine was admixed with 14 mg of 4-dimethylaminopyridine, 383 mg of (S)-2-tert-butoxycarbonylamino-3-methylbutanoic acid and 130 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and the mixture was stirred at 23° C. for 16 hours. The mixture was poured into water and extracted repeatedly with dichloromethane, and the combined organic extracts were washed with water and saturated sodium chloride solution and dried over sodium sulphate. The residue obtained after filtration and solvent removal was purified by chromatography. 314 mg (75%) of the title compounds were isolated as a colourless foam.

Workup

  1. extractionextracted repeatedly with dichloromethane
  2. washthe combined organic extracts were washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customThe residue obtained
  5. filtrationafter filtration and solvent removal
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-5b83573d0ec74444a5052df1968b0e0a
Source dataset
uspto-grants-2015_08
Patent number
US09096639B2

Reaction notes

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