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 1893039Notes

Reaction equation

HRID 1893039 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 vaccum 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 vaccum
  3. customto afford the crude product

Sources & evidence

ORD record
ord-7a97677cf01d48a58d5f46203e2cbd1f
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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