Triethylamine → HCID 67061890, Verbindung

HRID 910813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910813
[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@@H:16]([CH2:47][C:48](O)=[O:49])[CH2:15]2)=[CH:10][CH:9]=1.ClC(N(C)C)=C(C)C.[C:60]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])(=[O:63])[NH:61][NH2:62].CCN(CC)CC>C(Cl)Cl>[C:65]([O:64][C:60]([NH:61][NH:62][C:48](=[O:49])[CH2:47][C@H:16]1[CH2:15][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][O:6][CH2:5][C@@H:4]([CH3:51])[CH2:3][O:2][CH3:1])=[CH:9][CH:10]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:18][N:17]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])=[O:63])([CH3:68])([CH3:67])[CH3:66]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 67061895HCID 67061895, Verbindung

Produkt 1

HCID 67061890HCID 67061890, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1 mmol of [(2R,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetic acid (example 1g) in 5 ml of CH2Cl2 is treated at RT with 1.5 mmol of 1-chloro-N,N,2-trimethylpropenylamine, and stirred at RT for 2.5 h. This solution is added slowly, at 0° C., to a solution of 5 mmol of tert-butyl carbazate [870-46-2] and 5 mmol of Et3N in 1 ml of CH2Cl2. The reaction mixture is stirred at 4° C. for 16.5 h, then quenched with H2O. The aqueous layer is extracted with CH2Cl2 (2×). The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow oil. Rf=0.34 (EtOAc/Heptane 2:1); Rt=5.28 (gradient I).

Aufarbeitung

  1. stirringThe reaction mixture is stirred at 4° C. for 16.5 h
  2. customquenched with H2O
  3. extractionThe aqueous layer is extracted with CH2Cl2 (2×)
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography (SiO2 60 F)

Quellen und Nachweise

ORD-Eintrag
ord-fa8950b4ef2344b684f660fc98bb3744
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022068B2

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