Trifluoroacetic acid → HCID 68604780, compound

HRID 1593290Notes

Reaction equation

HRID 1593290 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 ((1S)-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 (M+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-5ba0fd0301594a948fe88d141482b647
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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