Di-tert-butyl dicarbonate → HCID 22219740, compound

HRID 1793859Notes

Reaction equation

HRID 1793859 reaction equation
CS(O)(=O)=O.[CH3:6][CH:7]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[NH2:8].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[Cl:34][C:35]1[N:36]=[C:37]2[N:41]([C:42]=1[S:43](Cl)(=[O:45])=[O:44])[CH:40]=[CH:39][S:38]2.CC(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1.O.CC(C)=O>[ClH:34].[Cl:34][C:35]1[N:36]=[C:37]2[N:41]([C:42]=1[S:43]([N:12]1[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH2:9][CH:7]([NH2:8])[CH3:6])=[CH:11]1)(=[O:45])=[O:44])[CH:40]=[CH:39][S:38]2

Participants

9

Reactant 5

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 6455349Methanesulfonic acid--1-(1H-indol-3-yl)propan-2-amine (1/1)HCID 23665647Potassium tert-butoxide

Product 1

HCID 22219740HCID 22219740, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of α-methyltryptamine methane sulfonate (5.0 g, 18.5 mmol) in a 1:1 mixture of acetone:water is treated with di-t-butyl dicarbonate (7.7 g, 55.5 mmol, 3 eq.), stirred at room temperature for 16 h, concentrated to an aqueous mixture and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo. A mixture of a portion of the resultant residue (2.0 g, 7.3 mmol, 1.1 eq.) and 6-chloroimidazo[2,1-b]thiazole-5-sulfonyl chloride (1.7 g, 6.6 mmol, 1.0 eq.) in THF is treated portionwise with potassium t-butoxide (820 mg, 7.3 mmol, 1.1 equiv.) at room temperature stirred for 1 h, poured into saturated NaHCO3 and extracted with EtOAc. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. This resultant residue is chromatographed (silica gel, 20%–50% EtOAc in hexanes as gradient eluent) to give the free base of the title product as a brown oil, 1.7 g (50% yield). Treatment with 4N HCl in dioxane and THF, followed by filtration and recrystallization of the filtercake from ethanol affords the title product as a light brown solid 1.0 g (40% yield), identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated to an aqueous mixture
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. stirringstirred for 1 h
  6. extractionextracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThis resultant residue is chromatographed (silica gel, 20%–50% EtOAc in hexanes as gradient eluent)

Sources & evidence

ORD record
ord-d57658c2151041e5ab15f824e837778d
Source dataset
uspto-grants-2006_04
Patent number
US07022701B2

Reaction notes

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