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Triethylamine → tert-Butyl {5-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]-2-thienyl}carbamate

HRID 446502
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 446502
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[F:31][C:32]([F:85])([F:84])[C:33]1[CH:34]=[C:35]([CH:77]=[C:78]([C:80]([F:83])([F:82])[F:81])[CH:79]=1)[C:36]([N:38]1[CH2:42][C@@:41]([CH2:50][CH2:51][N:52]2[CH2:57][CH2:56][C:55]3([C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[CH2:59][C@@H:58]3[O:66][CH2:67][C:68]([N:70]([CH3:76])[CH2:71][CH2:72][CH2:73][NH:74][CH3:75])=[O:69])[CH2:54][CH2:53]2)([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[O:40][CH2:39]1)=[O:37]>C(Cl)Cl>[F:83][C:80]([F:81])([F:82])[C:78]1[CH:77]=[C:35]([CH:34]=[C:33]([C:32]([F:31])([F:85])[F:84])[CH:79]=1)[C:36]([N:38]1[CH2:42][C@@:41]([CH2:50][CH2:51][N:52]2[CH2:53][CH2:54][C:55]3([C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[CH2:59][C@@H:58]3[O:66][CH2:67][C:68]([N:70]([CH3:76])[CH2:71][CH2:72][CH2:73][N:74]([CH3:75])[C:14]([C:12]3[S:13][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:11]=3)=[O:16])=[O:69])[CH2:56][CH2:57]2)([C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)[O:40][CH2:39]1)=[O:37]
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 221055695-(((Tert-butoxy)carbonyl)amino)thiophene-2-carboxylic acidHCID 866634192-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-[3-(methylamino)propyl]acetamide

Produkt 1

HCID 86663425
tert-Butyl {5-[{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}(methyl)carbamoyl]-2-thienyl}carbamate
Ausbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (94 mg, 0.385 mmol) obtained in Example 4c was dissolved in methylene chloride (4 mL), triethylamine (80 μL, 0.578 mmol) and pivaloyl chloride (52 μL, 0.424 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The compound (300 mg, 0.385 mmol) obtained in Example 1k was added to the reaction mixture under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v) to give the title compound (366 mg; yield, 94%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-4f4334251065464988c1d45db41cc2d7
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476253B2

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