Diisopropylethylamine → (9H-Fluoren-9-yl)methyl(S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamate

HRID 718913

Reaktionsgleichung

Reaktionsgleichung von HRID 718913
[S:1]1[CH:5]=[C:4]([CH2:6][NH:7][C@@H:8]([CH3:16])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[NH:21]([C:49]([O:51][CH2:52][CH:53]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[C:59]2[C:54]1=[CH:55][CH:56]=[CH:57][CH:58]=2)=[O:50])[C@H:22]([C:46](O)=[O:47])[CH2:23][C:24](=[O:45])[NH:25][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[S:1]1[CH:5]=[C:4]([CH2:6][N:7]([C@@H:8]([CH3:16])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])[C:46](=[O:47])[C@@H:22]([NH:21][C:49](=[O:50])[O:51][CH2:52][CH:53]2[C:65]3[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=3[C:59]3[C:54]2=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:23][C:24](=[O:45])[NH:25][C:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 640248Fmoc-Asn(Trt)-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67088371(S)-N-(benzo[b]thiophen-3-ylmethyl)-1,1-diethoxypropan-2-amine

Produkt 1

HCID 131730614(9H-Fluoren-9-yl)methyl(S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1,4-dioxo-4-(tritylamino)butan-2-ylcarbamateAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to the procedure described in the synthesis method of Compound III-1, (S)—N-(benzo[b]thiophen-3-ylmethyl)-1,1-diethoxypropan-2-amine (Compound IX-6) 13.2 g (45 mmol) and Fmoc-Asn(Trt)-OH 35.1 g (58.8 mmol) were dissolved in DMF (200 ml). HATU (25.6 g, 67.5 mmol) and DIEA (8.7 g, 67.5 mmol) were added at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into water (800 ml). The solution was extracted with EA (300 ml×3). The combined extracts were dried over Na2SO4 and then filtered. The solvent was removed in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=30:1 to 5:1 to give the title compound 22.0 g, (yield 56%).

Aufarbeitung

  1. extractionThe solution was extracted with EA (300 ml×3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel with PE

Quellen und Nachweise

ORD-Eintrag
ord-c8e75912638c4c439a67434cfbd33b58
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193734B2

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