Dichloromethane → HCID 10189838, compound

HRID 2289693Notes

Reaction equation

HRID 2289693 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:6]([O:12][S:13](=[O:34])(=[O:33])[NH:14][C:15](=[O:32])[CH2:16][C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][C:20]([CH:26]([CH3:28])[CH3:27])=[CH:19][C:18]=2[CH:29]([CH3:31])[CH3:30])=[C:5]([CH:35]([CH3:37])[CH3:36])[CH:4]=1)=O.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:60]CCl>>[ClH:60].[CH2:38]([NH:45][CH2:1][C:3]1[CH:4]=[C:5]([CH:35]([CH3:36])[CH3:37])[C:6]([O:12][S:13](=[O:33])(=[O:34])[NH:14][C:15](=[O:32])[CH2:16][C:17]2[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:20]([CH:26]([CH3:27])[CH3:28])=[CH:19][C:18]=2[CH:29]([CH3:31])[CH3:30])=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 54320995HCID 54320995, compound

Product 1

HCID 10189838HCID 10189838, compound

Procedure

[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-formyl-2,6-diisopropyl-phenyl ester (1.0 g, 1.9 mmol), benzylamine (0.21 mL, 1.9 mmol), and sodium triacetoxyborohydride (0.56 g, 2.6 mmol) were mixed in 100 mL of dichloromethane under a dry air atmosphere for 16 hours. Quenched by adding saturated sodium bicarbonate (50 mL). The resulting white solid was collected by filtration and resuspended in diethyl ether. HCl gas was bubbled through for 30 minutes, and the resulting solution was concentrated in vacuo to give the title compound as a white solid; mp 179-183° C.

Workup

  1. customQuenched
  2. additionby adding saturated sodium bicarbonate (50 mL)
  3. filtrationThe resulting white solid was collected by filtration
  4. customwas bubbled through for 30 minutes
  5. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3da003bd289a4a648de4710ff8cbe1a7
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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