Trifluoroacetic acid → (S)-N-((S)-5-((2-Chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamide

HRID 1055458Notes

Reaction equation

HRID 1055458 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[N:10]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])[C:11]2[C:16]([C:17]=1[CH2:18][N:19]1[C:25](=[O:26])[C@@H:24]([NH:27][C:28](=[O:40])[C@@H:29]([N:31](C)[C:32](=O)OC(C)(C)C)[CH3:30])[CH2:23][O:22][C:21]3[CH:41]=[CH:42][CH:43]=[CH:44][C:20]1=3)=[CH:15][CH:14]=[CH:13][CH:12]=2>C(Cl)Cl>[Cl:8][C:9]1[N:10]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])[C:11]2[C:16]([C:17]=1[CH2:18][N:19]1[C:25](=[O:26])[C@@H:24]([NH:27][C:28](=[O:40])[C@@H:29]([NH:31][CH3:32])[CH3:30])[CH2:23][O:22][C:21]3[CH:41]=[CH:42][CH:43]=[CH:44][C:20]1=3)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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)carbamate

Product 1

HCID 73055137(S)-N-((S)-5-((2-Chloro-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-2-(methylamino)propanamideYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was added to a solution of 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, 207 μmol, Eq: 1.00) in DCM (5 mL). The mixture was stirred at RT for 16 h, then concentrated. Sat. NaHCO3 was added to the residue and the mixture was extracted with DCM. The combined organic extracts were concentrated and the residue purified by preparative TLC to give the title compound (50 mg, 43%) as a white solid. MS m/z 529 (MH+)

Workup

  1. concentrationconcentrated
  2. additionSat. NaHCO3 was added to the residue
  3. extractionthe mixture was extracted with DCM
  4. concentrationThe combined organic extracts were concentrated
  5. customthe residue purified by preparative TLC

Sources & evidence

ORD record
ord-ba0e533605f44d49936ca04c10a372d2
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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