Trifluoroacetic acid → HCID 90037712, compound

HRID 1055487Notes

Reaction equation

HRID 1055487 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH3:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[CH2:19][N:20]1[C:26](=[O:27])[C@@H:25]([NH:28]C(=O)OC(C)(C)C)[CH2:24][O:23][C:22]2[C:36]([C:40]([F:43])([F:42])[F:41])=[CH:37][CH:38]=[CH:39][C:21]1=2>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[NH2:28][C@H:25]1[CH2:24][O:23][C:22]2[C:36]([C:40]([F:42])([F:41])[F:43])=[CH:37][CH:38]=[CH:39][C:21]=2[N:20]([CH2:19][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[CH:18][C:9]=2[CH3:8])[C:26]1=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90036405HCID 90036405, compound

Product 1

HCID 90037712HCID 90037712, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (533 μl) was added to a solution of (S)-tert-butyl 5-((2-methylnaphthalen-1-yl)methyl)-4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (71 mg, 142 μmol) in DCM (2 mL) at 0° C. After 2.5 h the mixture was concentrated and the residue azeotroped with MeCN to afford (S)-3-amino-5-((2-methylnaphthalen-1-yl)methyl)-9-(trifluoromethyl)-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one trifluoroacetate (73 mg, 100%) which was used without purification.

Workup

  1. concentrationAfter 2.5 h the mixture was concentrated
  2. customthe residue azeotroped with MeCN

Sources & evidence

ORD record
ord-0df5ddc4e45d46f982a0b9ee427a8a37
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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