Trifluoroacetic acid → HCID 68604780, compound

HRID 2267626Notes

Reaction equation

HRID 2267626 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:30]C(=O)OC(C)(C)C)[C:9](=[O:29])[NH:10][C@@H:11]2[C:17](=[O:18])[NH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[O:13][C@@H:12]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:30][C@@H:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([NH:10][C@@H:11]1[C:17](=[O:18])[NH:16][C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13][C@@H:12]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604634HCID 86604634, compound

Product 1

HCID 68604780HCID 68604780, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((1×)-1-(4-fluorophenyl)-2-oxo-2-{[(2R,3S)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]amino}ethyl)carbamate (65a) (202 mg, 0.400 mmol) was dissolved in 5:1 (v/v) dichloromethane: trifluoroacetic acid (4 mL) and kept at ambient temperature for 1 h. The solution was evaporated and the residue was dissolved in ethyl acetate and extracted with saturated aqueous sodium bicarbonate. The organic solution was dried and evaporated to afford the title compound (160 mg, 99%) as a yellow oil. MS APCI, m/z=406 (H+1). LC/MS: 1.60 min.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionextracted with saturated aqueous sodium bicarbonate
  4. customThe organic solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-82c0202bfe454cedb2f52a50c86d4d76
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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