HCID 10187839, compound → HCID 10186838, compound

HRID 2289694Notes

Reaction equation

HRID 2289694 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23][S:24](=[O:45])(=[O:44])[NH:25][C:26](=[O:43])[CH2:27][C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][C:31]([CH:37]([CH3:39])[CH3:38])=[CH:30][C:29]=2[CH:40]([CH3:42])[CH3:41])=[C:16]([CH:46]([CH3:48])[CH3:47])[CH:15]=1>ClCCl>[OH:12][CH2:13][C:14]1[CH:15]=[C:16]([CH:46]([CH3:47])[CH3:48])[C:17]([O:23][S:24](=[O:44])(=[O:45])[NH:25][C:26](=[O:43])[CH2:27][C:28]2[C:29]([CH:40]([CH3:41])[CH3:42])=[CH:30][C:31]([CH:37]([CH3:38])[CH3:39])=[CH:32][C:33]=2[CH:34]([CH3:36])[CH3:35])=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1

Participants

4

Reactant 2

HCID 10187839HCID 10187839, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10186838HCID 10186838, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.9 mL of a 1 M solution of diisobutyl aluminum hydride in dichloromethane was added to a solution of 3,5-Diisopropyl-4-{[(2,4,6-triisopropyl-phenyl)-acetyl]sulfamoyloxy}-benzoic acid methyl ester (1.0 g, 1.8 mmol) in 125 mL dichloromethane at -78° C. After 3 hours, the reaction was warmed to room temperature and then quenched with a saturated aqueous sodium sulfate solution. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated to give a white foam. Triturated with 10% diethyl ether/hexanes to give 0.29 g of the title compound as a white solid; mp 163-168° C.

Workup

  1. customquenched with a saturated aqueous sodium sulfate solution
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. customto give a white foam
  5. customTriturated with 10% diethyl ether/hexanes

Sources & evidence

ORD record
ord-f80f337d96884eab8efd2450a544850a
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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