Trifluoroacetic acid → (S)-N-[(S)-9-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-methylamino-propionamide trifluoroacetate

HRID 1055438Notes

Reaction equation

HRID 1055438 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([CH2:19][N:20]1[C:26](=[O:27])[C@@H:25]([NH:28][C:29](=[O:41])[C@@H:30]([N:32](C)[C:33](=O)OC(C)(C)C)[CH3:31])[CH2:24][O:23][C:22]3[CH:42]=[CH:43][CH:44]=[CH:45][C:21]1=3)=[C:14]([O:46][CH3:47])[CH:13]=[CH:12]2>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([CH2:19][N:20]1[C:21]3[CH:45]=[CH:44][CH:43]=[CH:42][C:22]=3[O:23][CH2:24][C@H:25]([NH:28][C:29](=[O:41])[C@@H:30]([NH:32][CH3:33])[CH3:31])[C:26]1=[O:27])=[C:14]([O:46][CH3:47])[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 72713381tert-butyl (S)-1-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Product 1

HCID 72712770(S)-N-[(S)-9-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-methylamino-propionamide trifluoroacetateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.48 g, 1 mL, 13.0 mmol, Eq: 153) was added to a solution of tert-butyl (S)-1-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (52 mg, 84.9 μmol, Eq: 1.00) in DCM and at 0° C. After 1 h the mixture was concentrated and the residue was triturated with Et2O to afford the title compound (30 mg, 58.5 μmol, 69.0%) as a light brown solid. MS m/z (MH+) 363.0

Workup

  1. concentrationAfter 1 h the mixture was concentrated
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-f4e83542d9c14a4aa5defa7c01b09c15
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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