Triethylamine → (6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl Ester

HRID 2403015Notes

Reaction equation

HRID 2403015 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:13][CH:12]([OH:14])[CH:11]([CH:15]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:16][CH:17]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:10]1)=[O:8].C(N(CC)CC)C.[CH3:47][C@@H:48]([C@@H:55]1[C@@:59]2([CH3:77])[CH2:60][CH2:61][CH:62]3[C@@:67]4([CH3:76])[CH2:68][CH2:69][CH:70]([O:72][C:73](Cl)=[O:74])[CH2:71][C:66]4=[CH:65][CH2:64][CH:63]3[CH:58]2[CH2:57][CH2:56]1)[CH2:49][CH2:50][CH2:51][CH:52]([CH3:54])[CH3:53].CO.C(Cl)(Cl)Cl>ClCCl>[CH3:47][CH:48]([CH:55]1[C:59]2([CH3:77])[CH:58]([CH:63]3[CH:62]([CH2:61][CH2:60]2)[C:67]2([CH3:76])[C:66]([CH2:71][CH:70]([O:72][C:73](=[O:74])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]4[CH2:13][CH:12]([OH:14])[CH:11]([CH:15]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[O:16][CH:17]([C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=5)[C:18]5[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=5)[CH2:10]4)=[O:8])[CH2:69][CH2:68]2)=[CH:65][CH2:64]3)[CH2:57][CH2:56]1)[CH2:49][CH2:50][CH2:51][CH:52]([CH3:53])[CH3:54]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 54236888C28H45ClO2HCID 1317282206-Amino-1-{3-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728221(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl EsterYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Referring to scheme 16, compound 65 (7.75 g, 14.5 mmol) was dissolved in anhydrous dichloromethane (50 mL) and cooled to 0° C. To the solution were added triethylamine (3 g, 4.2 mL, 30 mmol) and cholesteryl chloroformate (6.5 g, 29 mmol) successively. The reaction temperature was brought to ambient temperature and stirred further for 2 h. The completion of the reaction was ascertained by TLC (10% MeOH/CHCl3). The reaction mixture was evaporated under the vacuum to afford the crude product. Compound 66 (12.4 g, 88%) was obtained as a white foamy solid after column chromatography over silica gel using 3% MeOH/DCM.

Workup

  1. customwas brought to ambient temperature
  2. customThe reaction mixture was evaporated under the vacuum
  3. customto afford the crude product

Sources & evidence

ORD record
ord-09e5fb00fcbe481593f1d5d4837953ce
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

Loading…