Diisobutylaluminumhydride → HCID 118059881, compound

HRID 632532Notes

Reaction equation

HRID 632532 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[S:9]([N:12]([CH2:22][C:23](OCC)=[O:24])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][N:8]([S:9]([N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:22][CH:23]=[O:24])(=[O:11])=[O:10])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 118060108HCID 118060108, compound

Product 1

HCID 118059881HCID 118059881, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of ethyl [{[(tert-butoxycarbonyl)(4-methoxybenzyl)amino]sulfonyl}(4-methoxybenzyl)amino]acetate (5.30 g, 10 mmol) in dichloromethane (20.0 mL) at −78° C. under N2 was treated with 1.0 M diisobutylaluminum hydride in dichloromethane (12.2 mL, 12.2 mmol, 1.22 equiv.). The reaction mixture was stirred at −78° C. for 3 h. The reaction was then quenched with methanol (3 mL) and treated with dichloromethane (100 mL) and a saturated solution of sodium potassium tartrate (150 mL). This solution was stirred at room temperature overnight. The aqueous layer was then extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was washed with brine, dried over sodium sulfate and concentrated. The residue was then purified on silica gel (0-30% ethyl acetate/hexane gradient elution) to give the desired product (3.45 g, 71%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.24 (s, 1H), 7.23 (m, 4H), 6.88 (m, 4H), 4.68 (s, 2H), 4.31 (s, 2H), 4.07 (s, 2H), 3.72 (s, 3H), 3.71 (s, 3H), 1.40 (s, 9H).

Workup

  1. customThe reaction was then quenched with methanol (3 mL)
  2. additiontreated with dichloromethane (100 mL)
  3. stirringThis solution was stirred at room temperature overnight
  4. extractionThe aqueous layer was then extracted with dichloromethane (3×20 mL)
  5. washThe combined dichloromethane solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was then purified on silica gel (0-30% ethyl acetate/hexane gradient elution)

Sources & evidence

ORD record
ord-acc4f69f13f9424aae55229697f32d5e
Source dataset
uspto-grants-2016_04
Patent number
US09321755B2

Reaction notes

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