Acetic Acid → Xantocillin

HRID 736866Notes

Reaction equation

HRID 736866 reaction equation
[N+:1](/[C:3](/[C:19](/[N+:35]#[C-:36])=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([O:27][Si](C(C)(C)C)(C)C)=[CH:23][CH:22]=1)=[CH:4]\[C:5]1[CH:10]=[CH:9][C:8]([O:11][Si](C(C)(C)C)(C)C)=[CH:7][CH:6]=1)#[C-:2].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[N+:1](/[C:3](/[C:19](/[N+:35]#[C-:36])=[CH:20]/[C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)=[CH:4]\[C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)#[C-:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 16094285HCID 16094285, compound

Product 1

HCID 5378293XantocillinYield 119.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1Z,3Z)-2,3-diisocyano-1,4-bis(4-tert-butyldimethylsilyloxyphenyl)buta-1,3-diene (74.0 mg, 0.14 mmol) prepared in Reference Synthetic Example 10 was dissolved in tetrahydrofuran in nitrogen atmosphere, and acetic acid (21 ml, 0.36 mmol) was added under cooing with ice. Then, a 1.0 mol/l tetra-n-butylammonium fluoride/tetrahydrofuran solution (280 ml, 0.28 mmol) was slowly added dropwise. The reaction solution was returned to room temperature, followed by stirring for 3 hours, and the reaction solution was purified as it was by silica gel column chromatography (hexane:ethyl acetate=2:1) to give (1Z, 3Z)-2,3-diisocyano-1,4-bis(4-hydroxyphenyl)buta-1,3-diene (48.2 mg, 85%) as a yellow powder.

Workup

  1. additionwas added
  2. customwas returned to room temperature
  3. customthe reaction solution was purified as it

Sources & evidence

ORD record
ord-312dccf31fa14d77912f5a2b76ccfbd0
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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