Sodium hydride → HCID 18957769, compound

HRID 2379361Notes

Reaction equation

HRID 2379361 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[CH2:32][CH2:33][CH3:34]>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]([CH2:32][CH2:33][CH3:34])[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 24758Sodium hydrideHCID 336431-IodopropaneHCID 135624229HCID 135624229, compound

Product 1

HCID 18957769HCID 18957769, compoundYield 83%

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 [Example 5, Step 3] (1.48 g, 3.93 mmol) in anhydrous dimethylformamide (40 ml), cooled in an ice bath, was added sodium hydride (60% dispersion in oil, 173 mg, 4.33 mmol) and the resulting mixture stirred under nitrogen for 1 h. Iodopropane (0.46 ml, 4.72 mmol) was then added and the mixture stirred at room temperature for 3 h. The solvent was evaporated and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was re-extracted with more dichloromethane (100 ml), the organic extracts were combined, dried (MgSO4) and evaporated. The residue was then triturated with ether to afford the title compound (1.36 g, 83%) as a white solid. mp 138°14 140° C. 1H NMR (360 MHz, CDCl3) δ 0.80 (3H, t, J=7.4 Hz), 1.26-1.79 (8H, m), 1.94 (1H, m), 2.12 (1H, m), 3.30 (1H, m), 3.55 (1H, m), 4.29 (1H, m), 5.10 (2H, m), 5.13 (1H, d), 6.52 (1H, d, J=8.1 Hz), 7.23-7.34 (5H, m), 7.48 (1H, t of d, J=8.0 and 1.4 Hz), 7.56 (1H, dd, J=7.8 and 1.4 Hz).

Workup

  1. stirringthe mixture stirred at room temperature for 3 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between dichloromethane (100 ml) and water (100 ml)
  4. extractionThe aqueous layer was re-extracted with more dichloromethane (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was then triturated with ether

Sources & evidence

ORD record
ord-b32a04a463de4c4283075c2ae5604789
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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