Trifluoroacetic acid → HCID 67513954, compound

HRID 473903Notes

Reaction equation

HRID 473903 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C:16]=3[CH:29]=2)=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C.Cl[C:40]([O:42][CH2:43][CH:44]([CH3:46])[CH3:45])=[O:41].C(O)(C(F)(F)F)=O>ClCCl>[O:21]1[C:15]2[CH:14]=[CH:13][C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:2]4[N:3]([C:40]([O:42][CH2:43][CH:44]([CH3:46])[CH3:45])=[O:41])[CH:4]=[CH:5][N:1]=4)=[CH:7][CH:8]=3)=[CH:29][C:16]=2[CH2:17][NH:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 675152711,1-dimethylethyl 7-[4-(1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 67513954HCID 67513954, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl 7-[4-(1H-imidazol-2-yl)phenyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (490 mg, 1.25 mmol) was taken into dichloromethane (20 mL) followed by sequential addition of DIPEA (0.4 mL, 2.3 mmol) and isobutyl chloroformate (0.18 mL, 1.4 mmol) and the mixture was stirred at room temperature for 30 minutes. The mixture was concentrated then partitioned with ethyl acetate and 10% aqueous citric acid. The organic solution was washed with brine, dried over anhydrous sodium sulfate then filtered and concentrated. The residue thus obtained was taken into TFA (5 mL) and allowed to stand for 30 minutes at room temperature. The mixture was concentrated and the residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate and the organic solution was washed with brine, dried over anhydrous sodium sulfate then filtered and concentrated to give 2-methylpropyl 2-[4-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)phenyl]-1H-imidazole-1-carboxylate (361 mg, 65% yield). MS (EI) for C23H25N3O3: 392 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthen partitioned with ethyl acetate and 10% aqueous citric acid
  3. washThe organic solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthen filtered
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. waitto stand for 30 minutes at room temperature
  9. concentrationThe mixture was concentrated
  10. customthe residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate
  11. washthe organic solution was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationthen filtered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-748ab8ae7c14429a8e89a9318f140c8e
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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