Cesium carbonate → HCID 53988530, compound

HRID 341982Notes

Reaction equation

HRID 341982 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20](Cl)[C:21]4[CH:22]=[C:23]([C:27]([CH3:30])([CH3:29])[OH:28])[CH:24]=[CH:25][CH:26]=4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[SH:32][CH2:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36].C([O-])([O-])=O.[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([S:32][CH2:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:28])([CH3:30])[CH3:29])[CH:22]=4)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 15289599Ethyl 3-mercapto-2-methylpropanoateHCID 53988403HCID 53988403, compound

Product 1

HCID 53988530HCID 53988530, compoundYield 52%

Procedure

To the crude chloride of Step 4 dissolved in 10 mL of DNE, ethyl 3-mercapto-2-methylpropanoate (Step 6; 350 μl, approx. 2.4 mmol) and Cs2CO3 (1.61 g, 4.9 mmol) were added and the mixture was stirred at r.t. for 3.5 h. 25% Aq NH4OAc was then added and the reaction mixture was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using EtOAc:toluene 7.5:92.5 and 10:90 to yield 347 mg of the title compound as an oil (52% yield for Steps 6 and 7).

Workup

  1. additionwere added
  2. extractionthe reaction mixture was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-8b8685902ec845d69adb2c2ea30b08c7
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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