Methyl iodide → HCID 18957774, compound

HRID 2379364Notes

Reaction equation

HRID 2379364 reaction equation
[CH:1]1([C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:9](=[O:17])[CH:8]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH3:32]>CN(C)C=O>[CH:1]1([C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([CH3:32])[C:9](=[O:17])[CH:8]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135624229HCID 135624229, compound

Product 1

HCID 18957774HCID 18957774, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-cyclopentyl-1,3-dihydro-3(R,S)-[(benzyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (1.47 g, 3.91 mmol) in anhydrous dimethylformamide (40 ml) under nitrogen, cooled in an ice bath, was added sodium hydride (55% dispersion in oil, 178 mg, 4.08 mmol) in portions and the resulting mixture stirred for lb. Iodomethane (0.26 ml, 4.1 mmol) was then added and the mixture stirred for 30 min. The solvent was evaporated and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The aqueous layer was re-extracted with dichloromethane (20 ml), the organic extracts were combined, dried (MgSO4), and evaporated. The residue was triturated with diethyl ether to afford the title compound (1.19 g, 78%) as a white solid. 1H NMR (360 MHz, CDCl3) δ 1.26 (1H, m), 1.46-2.00 (6H, m), 2.00-2.20 (1H, m), 3.30 (1H, m), 3.40 (3H, s), 5.08 (2H, d, J=1.4 Hz), 5.15 (1H, d, J=8 Hz.), 6.50 (1H, d, J=8 Hz), 7.24-7.62 (9H, m).

Workup

  1. stirringthe mixture stirred for 30 min
  2. customThe solvent was evaporated
  3. customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
  4. extractionThe aqueous layer was re-extracted with dichloromethane (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8d51ddb46d504be08759a1314d7b634f
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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