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

Trifluoroacetic acid → (S)-N-((3S,4S)-1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino) propanamide 2,2,2-trifluoroacetate

HRID 1486051
Notes
Print preview

Reaction equation

HRID 1486051 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:14][N:15]3[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:36])[C@@H:25]([N:27](C)[C:28](=O)OC(C)(C)C)[CH3:26])[C@H:19]([CH3:37])[N:18]([C:38](=[O:44])[CH2:39][S:40]([CH3:43])(=[O:42])=[O:41])[C:17]4[CH:45]=[CH:46][CH:47]=[CH:48][C:16]3=4)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50]>C(Cl)Cl>[F:52][C:51]([F:54])([F:53])[C:49]([OH:55])=[O:50].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:14][N:15]3[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:36])[C@@H:25]([NH:27][CH3:28])[CH3:26])[C@H:19]([CH3:37])[N:18]([C:38](=[O:44])[CH2:39][S:40]([CH3:43])(=[O:42])=[O:41])[C:17]4[CH:45]=[CH:46][CH:47]=[CH:48][C:16]3=4)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118292599tert-butyl(S)-1-((3S,4S)-1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Product 1

HCID 73427176(S)-N-((3S,4S)-1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino) propanamide 2,2,2-trifluoroacetateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a rt solution of tert-butyl(S)-1-((3S,4S)-1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (42.7 mg, 62.4 μmol) in CH2Cl2 (249 μl) was added TFA (62.4 μl). The reaction was stirred at rt for 1.5 h, then concentrated, taken up in H2O, and lyophilized to provide (S)-N-((3S,4S)-1-((7-methoxy-2-oxo-2H-chromen-4-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino) propanamide 2,2,2-trifluoroacetate (41.2 mg, 95%) as a white solid. MS m/z 585 (MH)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e78d84314750404bb2cd160a09fa1983
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422331B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes