Reaction #11690

ord-bce1a18b501744319de4def70546e546

Reaction equation

C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)OC(C)(C)C
(2S,3S)-3-t-butyloxycarbonylamino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one
C1CCOC1.ClCCl.O=C(O)C(F)(F)F
trifluoroacetic acid dichloromethane tetrahydrofuran
→
C[C@@H]1Oc2ccccc2NC(=O)[C@H]1N.O=C(O)C(F)(F)F
(2S,3S)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt

Reactants

C[C@@H]1Oc2ccccc2NC(=O)[C@H]1NC(=O)OC(C)(C)C
(2S,3S)-3-t-butyloxycarbonylamino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one
C1CCOC1.ClCCl.O=C(O)C(F)(F)F
trifluoroacetic acid dichloromethane tetrahydrofuran

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherfollowed by solvent evaporation and coevaporation with tetrahydrofuran under vacuum

Procedure

(2S,3S)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt was prepared from (2S,3S)-3-t-butyloxycarbonylamino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Rob, et al., Bioorg. & Med. Chem. Lett. 1994, 4, 1789–1794) by treatment with a solution of trifluoroacetic acid-dichloromethane-tetrahydrofuran (1:10:10) at room temperature, followed by solvent evaporation and coevaporation with tetrahydrofuran under vacuum.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07098235B2uspto-grants-2006_08