Methyl iodide → HCID 69686346, compound

HRID 2231085Notes

Reaction equation

HRID 2231085 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH:7]([N:9]1[C:15](=[O:16])[CH:14]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH2:13][CH2:12][C:11](=[O:28])[NH:10]1)[CH3:8])(C)(C)[CH3:2].[C:30]([O-])([O-])=O.[K+].[K+].IC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1COCC1.ClCCl>[CH2:1]([O:5][C:6](=[O:29])[CH:7]([N:9]1[C:15](=[O:16])[CH:14]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])[CH2:13][CH2:12][C:11](=[O:28])[N:10]1[CH3:30])[CH3:8])[CH3:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69686120HCID 69686120, compound

Product 1

HCID 69686346HCID 69686346, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-propionic acid tert-butyl ester (14) (314 mg, 0.84 mmol), benzyltriethylammonium chloride (30 mg, 0.13 mmol), K2CO3 (406 mg, 2.94 mmol) and iodomethane (360 mg, 2.53 mmol) in THF (8 mL) was stirred at room temperature for five days. The mixture was diluted with dichloromethane (70 mL), washed with water three times, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to dryness to afford 296 mg (91% yield) of the title compound as a mixture of diastereomers. 1H-NMR (500 MHZ, CDCl3) δ 1.25-1.35 (m, 2.5H), 1.47-1.52 (m, 0.5H), 1.60-1.75 (m, 3H), 2.37-2.52 (m, 2H), 3.05-3.14 (m, 0.5H), 3.30-3.45 (m, 3.5H), 3.45-3.58 (m, 1H), 4.14-4.28 (m, 2H), 4.52-4.58 (m, 0.5H), 4.80-4.87 (m, 0.5H), 5.13-5.28 (m, 1H), 7.70-7.90 (m, 4H). Analytical HPLC: 6.00 and 6.11 min. LC-MS (ES+): m/e=388 (M+H+).

Workup

  1. washwashed with water three times
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-003c257a4b83483cb35273da93b0a3bc
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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