Trifluoroacetic acid → (S)-3-amino-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one trifluoroacetate

HRID 1055359Notes

Reaction equation

HRID 1055359 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][O:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[NH2:9][C@H:8]1[CH2:7][O:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

Product 1

HCID 69197641(S)-3-amino-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (2 g, 7.19 mmol, Eq: 1.00) in DCM (16.7 mL) at 0° C. was added trifluoroacetic acid (TFA, 16.4 g, 10.7 mL, 144 mmol, Eq: 20.00). After 1 h the mixture was concentrated, and the residue was triturated with 5 mL of Et2O and 35 ml of pentane to give a gum. The solution was removed and this gummy residue material was dried to give the title compound (2.1 g) as a pink foam which was used without purification.

Workup

  1. concentrationAfter 1 h the mixture was concentrated
  2. customthe residue was triturated with 5 mL of Et2O and 35 ml of pentane
  3. customto give a gum
  4. customThe solution was removed
  5. customthis gummy residue material was dried

Sources & evidence

ORD record
ord-d247514ee171435a88c34547c51b8749
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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