Hydrochloric Acid → HCID 131714829, compound

HRID 365041Notes

Reaction equation

HRID 365041 reaction equation
C(/[C:11]1[CH:26]=[CH:25][C:14]([C:15](N(O)CCCC(O)=O)=[O:16])=[CH:13][CH:12]=1)=C/CCCCCCCC.[OH-:27].[CH2:28]([N+:32]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31].Cl.[O:46]1[CH2:51][CH2:50]OCC1>>[CH2:41]([N+:32]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:42][CH2:43][CH3:44].[CH2:15]([O:16][NH:32][CH2:28][CH2:29][CH2:50][C:51]([O-:46])=[O:27])[C:14]1[CH:13]=[CH:12][CH:11]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 2723671Tetrabutylammonium HydroxideHCID 13672802HCID 13672802, compound

Product 1

HCID 131714829HCID 131714829, compound

Procedure

To a stirred solution of the compound prepared in Example 3 Part B (5.74 g, 30.0 mM) in dioxane (50 ml) was added tetrabutylammonium hydroxide (36 mM, 23.4 ml of a 40% solution) under argon and the mixture stirred at room temperature overnight. Excess base was neutralized with 1.0N HCl (6 ml, 6 mM) and then the crude mixture was evaporated. Residue was azeotroped (4×) with CH3CN to insure dryness, then stored under vacuum. TLC (9:1) CH2Cl2 --CH3OH, Rf product=0.48, UV and PMA, single spot.

Workup

  1. customthe crude mixture was evaporated
  2. customResidue was azeotroped (4×) with CH3CN

Sources & evidence

ORD record
ord-691b202946cc438a98f62ccefe95435c
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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