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

HRID 718907

반응식

HRID 718907 반응식
[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:27]([O:29][CH2:30][CH:31]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28])[C@H:22]([C:24](O)=[O:25])[CH3:23].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:24](=[O:25])[C@@H:22]([NH:21][C:27](=[O:28])[O:29][CH2:30][CH:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:38]3[C:43]2=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH3:23])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineHCID 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

생성물 1

HCID 86652579(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamate수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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-Ala-OH 18.3 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 16.9 g, (yield 64%).

후처리

  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

출처 및 근거

ORD 기록
ord-34381bded0034e55988a634465e4bf03
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193734B2

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