Iodoethane → HCID 66757688, compound

HRID 242628Notes

Reaction equation

HRID 242628 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=3[NH:16][C:15](=[O:25])[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:28](I)[CH3:29]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=3[N:16]([CH2:28][CH3:29])[C:15](=[O:25])[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66758207HCID 66758207, compound

Product 1

HCID 66757688HCID 66757688, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-3-(8-Chloro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (0.258 g, 0.70 mmol) was dissolved in THF (7 mL) and cooled to 0° C. To the solution was added NaH (0.042 g, 1.0 mmol) and stirred for 15 min, followed by ethyl iodide (0.085 mL, 1.0 mmol). The solution was allowed to warm to room temperature slowly and stir at room temperature for 14 h. The reaction was quenched with water and extracted with EtOAc (3×). The organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (75% ethyl acetate/25% ethyl acetate to 100% ethyl acetate) to yield the title compound (0.130 g, 47%). 1H-NMR (CDCl3): δ 1.16 (t, 3H), 1.43 (s, 9H), 1.75 (sextet, 1H), 2.18 (pentet, 1H), 3.05-3.9 (m, 1H), 7.20 (m, 3H). ESI-MS m/z: 394 (M+1), retention time 2.25.

Workup

  1. temperatureto warm to room temperature slowly
  2. stirringstir at room temperature for 14 h
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc (3×)
  5. customThe organics were collected together
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. custompurified by Biotage flash chromatography (75% ethyl acetate/25% ethyl acetate to 100% ethyl acetate)

Sources & evidence

ORD record
ord-02afa449a0ca4187a0a843764136c01d
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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