Chloride → 1,10-Bis(3',5'-dimethyl-4'-hydroxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane

HRID 2288252Notes

Reaction equation

[Cl-].[CH3:2][C:3]1[CH:4]=[C:5]([C:14]([N:16]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][N:25]([C:34]([C:36]3[CH:41]=[C:40]([CH3:42])[C:39]([O:43]C(=O)C)=[C:38]([CH3:47])[CH:37]=3)=[O:35])[CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([CH3:13])[C:8]=1[O:9]C(=O)C.C[O-].[Na+]>CO>[CH3:13][C:7]1[CH:6]=[C:5]([C:14]([N:16]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][N:25]([C:34]([C:36]3[CH:41]=[C:40]([CH3:42])[C:39]([OH:43])=[C:38]([CH3:47])[CH:37]=3)=[O:35])[CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])[CH:4]=[C:3]([CH3:2])[C:8]=1[OH:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To 40 ml of mixed solvent of anhydrous methanolmethylene chloride was dissolved 0.5 g/0.8 mmol of 1,10-bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane, and the solution was cooled to 0° C. To this solution was added 2.6 ml of freshly prepared 1M methanol solution of sodium methoxide, and the mixture was stirred at 0° C. for 2 hours. After adding Amberlite 15 until the reaction solution became neutral, the resin was separated by filtration and the filtrate was concentrated under reduced pressure to obtain 0.4 g of 1,10-bis(3',5'-dimethyl-4'-hydroxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane. 1H-NMR (CDCl3): δ2.15 (12H, s), 3.6 (16H, br), 3.8 (8H, br), 5.89 (2H, s), 6.90 (4H, s).

Workup

additionAfter adding Amberlite 15 until the reaction solution
customthe resin was separated by filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0a4dbd4e19074b6b8e0164b1b9069a4b
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087502

Reaction notes

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