Triethylamine → HCID 131728209, compound

HRID 1893017Notes

Reaction equation

HRID 1893017 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])[CH2:11][CH:10]1[CH:15]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:16][CH:17]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:8].C(N([CH2:45][CH3:46])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)CCCC(C)C.CO.C(Cl)(Cl)Cl>ClCCl>[CH3:76][C:67]12[CH2:68][CH2:69][CH:70]([O:72][C:73](=[O:74])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]3[CH2:13][CH:12]([OH:14])[CH2:11][CH:10]3[CH:15]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[O:16][CH:17]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[O:8])[CH2:71][C:66]1=[CH:65][CH2:64][CH:63]1[CH:62]2[CH2:61][CH2:60][C:59]2([CH3:77])[CH:58]1[CH2:57][CH2:56][CH:55]2[CH2:48][CH2:47][CH2:2][CH2:3][CH2:4][CH2:5][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 54236888C28H45ClO2HCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728209HCID 131728209, compoundYield 187%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Referring to scheme 2, compound 5 (13.3 g, 25 mmol) was dissolved in anhydrous dichloromethane (100 mL) and cooled to 0° C. To the solution were added triethylamine (7.5 g, 10 mL, 75 mmol) and cholesteryl chloroformate (11.24 g, 25 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 6 (22.1 g, 93%) was obtained as a white foamy solid after column chromatography over silica gel.

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-ecb9e0542f0849a09a1c595563264c37
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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