Toluene → tert-butyl (S)-1-((S)-5-((2-chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

HRID 1055457노트

반응식

HRID 1055457 반응식
N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.[CH3:20][N:21]([C@@H:29]([CH3:45])[C:30](=[O:44])[NH:31][C@H:32]1[CH2:38][O:37][C:36]2[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=2[NH:34][C:33]1=[O:43])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].[Cl:46][C:47]1[N:48]([C:58]2[CH:65]=[CH:64][CH:63]=[CH:62][C:59]=2[C:60]#[N:61])[C:49]2[C:54]([C:55]=1[CH2:56]O)=[CH:53][CH:52]=[CH:51][CH:50]=2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CO>[Cl:46][C:47]1[N:48]([C:58]2[CH:65]=[CH:64][CH:63]=[CH:62][C:59]=2[C:60]#[N:61])[C:49]2[C:54]([C:55]=1[CH2:56][N:34]1[C:33](=[O:43])[C@@H:32]([NH:31][C:30](=[O:44])[C@@H:29]([N:21]([CH3:20])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])[CH3:45])[CH2:38][O:37][C:36]3[CH:39]=[CH:40][CH:41]=[CH:42][C:35]1=3)=[CH:53][CH:52]=[CH:51][CH:50]=2

참가 물질

8

반응물 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 72713380tert-Butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamateHCID 900376432-(2-Chloro-3-(hydroxymethyl)-1H-indol-1-yl)benzonitrile

생성물 1

HCID 131736361tert-butyl (S)-1-((S)-5-((2-chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate수율 50%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Diethyl azodicarboxylate solution 40 wt. % in toluene (DEAD 40% w/w, 360 mg, 377 μl, 828 μmol, Eq: 2) was added to a solution of tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate (226 mg, 621 μmol, Eq: 1.5), 2-(2-chloro-3-(hydroxymethyl)-1H-indol-1-yl)benzonitrile (117 mg, 414 1=01, Eq: 1.00) and Ph3P (217 mg, 828 μmol, Eq: 2) in THF (5 mL) and the mixture was stirred at RT for 2.5 d. The mixture was diluted with MeOH (10 mL), concentrated and the residue purified by preparative TLC to give tert-butyl (S)-1-((S)-5-((2-chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (130 mg, 50%) as a yellow solid.

후처리

  1. concentrationconcentrated
  2. customthe residue purified by preparative TLC

출처 및 근거

ORD 기록
ord-aa447dff82e14216abea7647dff92d56
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394263B2

반응 노트

불러오는 중…