5-Chloro-3-methyl-1,2,4-thiadiazole → HCID 59378062, compound

HRID 1639570Notes

Reaction equation

HRID 1639570 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:8].Cl[C:33]1[S:37][N:36]=[C:35]([CH3:38])[N:34]=1>O1CCCC1>[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([C:33]1[S:37][N:36]=[C:35]([CH3:38])[N:34]=1)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH3:8]

Participants

5

Reactant 3

HCID 129191595-Chloro-3-methyl-1,2,4-thiadiazoleHCID 23557313HCID 23557313, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59378062HCID 59378062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (12.2 g, 0.11 mol) followed by 2-tert-butoxycarbonyloctanedioic acid 1-tert-butyl ester 8-ethyl ester (2021037) (30.0 g, 83.8 mmol) was added portionwise to stirred tetrahydrofuran (170 mL) and then 5-chloro-3-methyl-1,2,4-thiadiazole (2009380) (11.3 g, 83.8 mmol) was added to the resultant slurry. The mixture was heated at reflux overnight before being quenched with water (150 mL) and extracted with dichloromethane (3×200 mL). The combined organic fractions were dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (6:1 hexane/ethyl acetate) to afford 2-tert-butoxycarbonyl-2-(3-methyl[1,2,4]thiadiazol-5-yl)octanedioic aAcid 1-tert-butyl ester 8-ethyl ester (2021038) (10 g, 26%) as a yellow oil.

Workup

  1. additionwas added portionwise
  2. temperatureThe mixture was heated
  3. temperatureat reflux overnight
  4. custombefore being quenched with water (150 mL)
  5. extractionextracted with dichloromethane (3×200 mL)
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified by flash chromatography (6:1 hexane/ethyl acetate)
  9. customto afford 2-tert-butoxycarbonyl-2-(3-methyl[1,2,4]thiadiazol-5-yl)octanedioic aAcid 1-tert-butyl ester 8-ethyl ester (2021038) (10 g, 26%) as a yellow oil

Sources & evidence

ORD record
ord-d3f2baac8b764927a7043c35ee5d164b
Source dataset
uspto-grants-2012_02
Patent number
US08110577B2

Reaction notes

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