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

HRID 1055364Notes

Reaction equation

HRID 1055364 reaction equation
[CH3:1][C@H:2]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4](=[O:13])[C@H:3]1[NH:14]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:14][C@@H:3]1[C:4](=[O:13])[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[O:8][C@@H:2]1[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54137235((6R,7S)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester

Product 1

HCID 67076981(2R,3S)-3-amino-2-methyl-2,3-dihydrobenzo[b][1,4]-oxazepin-4 (5H)-oneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R,3S)-2-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (0.65 g, 2.22 mmol, Eq: 1.00) in DCM (11.2 mL) at 0° C. was added TFA (12.7 g, 8.26 mL, 111 mmol, Eq: 50.00). After 1 h the mixture was concentrated, the residue dissolved in 50 mL DCM and washed with sat. NaHCO3. The NaHCO3 mixture was extracted with DCM and the combined extracts dried over Na2SO4, filtered and concentrated to afford the title compound (0.42 g, 96%) as a yellow foam which was used without purification.

Workup

  1. concentrationAfter 1 h the mixture was concentrated
  2. dissolutionthe residue dissolved in 50 mL DCM
  3. washwashed with sat. NaHCO3
  4. extractionThe NaHCO3 mixture was extracted with DCM
  5. dry with materialthe combined extracts dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc7e38e3152946ddba223f7b91f6712d
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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