Trifluoroacetic acid → HCID 58997958, compound

HRID 2267624Notes

Reaction equation

HRID 2267624 reaction equation
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]1[C:23](=[O:24])[NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[O:19][C@@H:18]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:24]=[C:23]1[NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[O:19][C@H:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:17]1[NH:16][C:14](=[O:15])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58997963HCID 58997963, compound

Product 1

HCID 58997958HCID 58997958, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N2-[tert-Butoxycarbonyl]-N1-[(2R,3S)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]-L-leucinamide (64f) (83 mg, 0.177 mmol) was dissolved in 5:1 (v/v) dichloromethane:trifluoroacetic acid and kept at ambient temperature for 1 h. The solution was evaporated and the residue dissolved in ethyl acetate. The solution was extracted in succession with saturated aqueous sodium bicarbonate and brine then the organic solution was dried, filtered and evaporated to afford the title compound (65 mg, 99%) as a yellow oil. MS APCI, m/z=368 (M+1). LC/MS: 1.63 min.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionThe solution was extracted in succession with saturated aqueous sodium bicarbonate and brine
  4. customthe organic solution was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-605f5d3c9b7840f7884a644c7edc9f3c
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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