Triethylamine → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl Ester

HRID 1893021Notes

Reaction equation

HRID 1893021 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(CC)CC)C.[CH2:47]([C:63]1([CH3:90])[CH2:72][CH2:71][C:70]2[C:65](=[C:66]([CH3:89])[C:67]([CH3:88])=[C:68]([O:74][CH2:75][CH2:76][O:77][C:78](=O)[O:79]N3C(=O)CCC3=O)[C:69]=2[CH3:73])[O:64]1)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62].CO.C(Cl)(Cl)Cl>ClCCl>[CH2:47]([C:63]1([CH3:90])[CH2:72][CH2:71][C:70]2[C:65](=[C:66]([CH3:89])[C:67]([CH3:88])=[C:68]([O:74][CH2:75][CH2:76][O:77][C:78](=[O:79])[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])[C:69]=2[CH3:73])[O:64]1)[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 59347260Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl EsterHCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728212(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl EsterYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Amine 5 (8.7 g, 16.3 mmol) was dissolved in anhydrous dichloromethane (40 mL) and cooled to 0° C. To the solution were added triethylamine (5.06 g, 6.73 mL, 50 mmol) and compound 18 (10 g, 16.2 mmol) successively. The reaction temperature was brought to ambient temperature and stirred further for 6 h. The completion of the reaction was ascertained by TLC (10% MeOH/CHCl3). The reaction mixture was diluted with dichloromethane and washed with saturated NaHCO3, water followed by brine. The organic layer was dried over sodium sulfate, filtered and concentrated under vacuum to afford the crude product. Compound 19 (14.5 g, 88%) was obtained as a white foamy solid after column chromatography over silica gel.

Workup

  1. customwas brought to ambient temperature
  2. washwashed with saturated NaHCO3, water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product

Sources & evidence

ORD record
ord-b1597eeaf96a4b72800e1bf4ec72c091
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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