HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

HCID 178455980, compound → tert-butyl (2S,5S)-2-[9-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-isoleucyl]-5-methylpyrrolidin-2-yl}-1H-imidazol-5-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidine-1-carboxylate

HRID 590678
Notes
Print preview

Reaction equation

HRID 590678 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[C@@H:17]([CH3:18])[CH2:16][CH2:15][C@H:14]1[C:19]1[NH:20][C:21]([C:24]2[CH:29]=[C:28]3[CH2:30][O:31][C:32]4[CH:57]=[C:56]5[C:35]([CH2:36][CH2:37][C:38]6[N:42]=[C:41]([C@@H:43]7[CH2:47][CH2:46][C@H:45]([CH3:48])[N:44]7[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:40][C:39]=65)=[CH:34][C:33]=4[C:27]3=[CH:26][CH:25]=2)=[CH:22][N:23]=1)=[O:12])[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4]>ClCCl.O=[Mn]=O>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[C@@H:17]([CH3:18])[CH2:16][CH2:15][C@H:14]1[C:19]1[NH:20][C:21]([C:24]2[CH:29]=[C:28]3[CH2:30][O:31][C:32]4[CH:57]=[C:56]5[C:35]([CH:36]=[CH:37][C:38]6[N:42]=[C:41]([C@@H:43]7[CH2:47][CH2:46][C@H:45]([CH3:48])[N:44]7[C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[NH:40][C:39]=65)=[CH:34][C:33]=4[C:27]3=[CH:26][CH:25]=2)=[CH:22][N:23]=1)=[O:12])[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 178455980HCID 178455980, compound

Product 1

HCID 178455982tert-butyl (2S,5S)-2-[9-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-isoleucyl]-5-methylpyrrolidin-2-yl}-1H-imidazol-5-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidine-1-carboxylateYield 40.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of tert-butyl (2S,5S)-2-[9-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-isoleucyl]-5-methylpyrrolidin-2-yl}-1H-imidazol-5-yl)-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidine-1-carboxylate (2.77 g, 3.5 mmol) in dichloromethane (25 mL) was added MnO2 (9.00 g, 103 mmol). The resulting slurry was stirred at room temperature for 20 h. The solution was diluted with dichloromethane, filtered through celite, and concentrated. The crude oil was purified by column chromatography (SiO2, 0-5-10% EtOAc/MeOH) to provide tert-butyl (2S,5S)-2-[9-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-isoleucyl]-5-methylpyrrolidin-2-yl}-1H-imidazol-5-yl)-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidine-1-carboxylate (1.10 g, 40% over 2 steps) as a brown foam. LCMS-ESI+: calc'd for C44H53N7O6: 775.41 (M+). Found: 776.37 (M+H+)

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe crude oil was purified by column chromatography (SiO2, 0-5-10% EtOAc/MeOH)

Sources & evidence

ORD record
ord-da0c0d8101574233b3f1817f7c2405d7
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09233974B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes