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Isobutyl iodide → 1,3-Dihydro-5-(1,1-dimethylethyl)1-(2-Methylpropyl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4benzodiazepin-2-one

HRID 2399686
Notes
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Reaction equation

HRID 2399686 reaction equation
[CH3:1][C:2]([C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8](=[O:16])[CH:7]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:6]=1)([CH3:4])[CH3:3].[H-].[Na+].[CH3:30][CH:31]([CH3:34])[CH2:32]I>CN(C)C=O>[CH3:4][C:2]([C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:30][CH:31]([CH3:34])[CH3:32])[C:8](=[O:16])[CH:7]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[N:6]=1)([CH3:1])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 135722083HCID 135722083, compound

Product 1

HCID 101369981,3-Dihydro-5-(1,1-dimethylethyl)1-(2-Methylpropyl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4benzodiazepin-2-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

A solution of 1,3-dihydro-5-(1,1-dimethylethyl)-3(R,S) -[(benzyloxycarbonyl)-amino]-2H-1,4-benzodiazepin-2-one (500 mg, 1.4 mmol) in dimethylformamide (10 ml) under an atmosphere of nitrogen, was treated with sodium hydride (54 mg of a 57% dispersion in mineral oil, 1.4 mol) in one portion at 0° C. After 1 h, 2-methylpropyl iodide (0.17 ml, 1.45 mmol) was added and the resulting mixture stirred at room temperature for 16 h. The solvent was then evaporated and the crude residue partitioned between water (15 ml) and dichloromethane (2×20 ml). The combined organic phases were washed with brine (2×20 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica using 2:1 petrol:ethyl acetate as eluent, to afford the title compound as a colourless solid (320 mg, 56%). 1H NMR (250 MHz, D6 -DMSO) δ 0.63 (3H, d, J=7 Hz), 0.77 (3H, d, J=7 Hz), 1.26 (9H, s), 1.49 (1H, m), 3.56 (1H, dd, J=4 Hz, 14 Hz), 4.10 (1H, dd, J=4 Hz, 14 Hz), 4.88 (1H, m), 5.02 (2H, m), 7.20-7.40 (5H, m), 7.58 (1H, t, J=8 Hz), 7.66 (1H, d, J=9 Hz), 7.77 (1H, d, J=8 Hz), 8.18 (1H, d, J=9 Hz).

Workup

  1. customThe solvent was then evaporated
  2. customthe crude residue partitioned between water (15 ml) and dichloromethane (2×20 ml)
  3. washThe combined organic phases were washed with brine (2×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica using 2:1 petrol

Sources & evidence

ORD record
ord-a07045179234472ea70bb1f9bbe439ac
Source dataset
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05451582

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes