Potassium Iodide → HCID 90231437, compound

HRID 1481898Notes

Reaction equation

HRID 1481898 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[CH3:43].[I-].[K+]>O1CCCC1.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][C:34]=2[CH3:43])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 811061-Chloromethyl-2-methylnaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate2×

Product 1

HCID 90231437HCID 90231437, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3.0 g (10.83 mmol) ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (Intermediate 2) in 55 mL of anhydrous tetrahydrofuran at −78° C. was added slowly a solution of 1 M lithium bis(trimethylsilyl)amide in tetrahydrofuran (24 mL, 24 mmol). The solution was stirred at −78° C. for 30 min. A solution of 5.35 g (28.2 mmol) 1-chloromethyl-2-methyl-naphthalene in 15 mL of tetrahydrofuran was slowly added. The reaction mixture was stirred at −78° C. for 10 min, the cooling bath was removed and the mixture stirred overnight. Potassium iodide (1.8 g, 10.83 mmol) was added to the mixture. After 2 h, water and ethyl acetate were added to the mixture, the organic layer was washed with 10% aqueous sodium bisulfate, brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated. The residue was purified by silica gel chromatography to afford the title compound (3.2 g) as a light yellow solid. LC-MS: 432 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 10 min
  2. customthe cooling bath was removed
  3. stirringthe mixture stirred overnight
  4. waitAfter 2 h
  5. washthe organic layer was washed with 10% aqueous sodium bisulfate, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-88813fc7e708436aaf2119dd0167acb9
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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