Diethyl Ether → HCID 22710252, compound

HRID 352977Notes

Reaction equation

HRID 352977 reaction equation
C(OC([NH:8][S:9]([CH:12]1[NH:17][CH2:16][C:15]2[S:18][C:19]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([C:32]4[NH:33][C:34]5[C:39]([CH:40]=4)=[CH:38][C:37]([Cl:41])=[CH:36][CH:35]=5)(=[O:31])=[O:30])[CH2:25][CH:24]3[CH2:42][C:43]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)=[O:44])=[O:22])=[N:20][C:14]=2[CH2:13]1)(=[O:11])=[O:10])=O)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)C>C(Cl)Cl>[NH2:8][S:9]([CH:12]1[NH:17][CH2:16][C:15]2[S:18][C:19]([C:21]([N:23]3[CH2:28][CH2:27][N:26]([S:29]([C:32]4[NH:33][C:34]5[C:39]([CH:40]=4)=[CH:38][C:37]([Cl:41])=[CH:36][CH:35]=5)(=[O:31])=[O:30])[CH2:25][CH:24]3[CH2:42][C:43]([N:45]3[CH2:46][CH2:47][O:48][CH2:49][CH2:50]3)=[O:44])=[O:22])=[N:20][C:14]=2[CH2:13]1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 22709624HCID 22709624, compound

Product 1

HCID 22710252HCID 22710252, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In methylene chloride (3 ml) was dissolved 1-[[6-(tert-butoxycarbonylaminosulfonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]-2-[[(morpholin-4-yl)carbonyl]methyl]piperazine (275 mg), followed by the addition of trifluoroacetic acid (3 ml). The resulting mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure. A saturated solution of hydrochloride. in ethanol (3 ml) was added and the resulting mixture was stirred at room temperature for 1.5 hours. The residue obtained by distilling off the solvent under reduced pressure was added with methylene chloride and water to separate into layers. The water layer was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by preparative thin-layer chromatography (methanol:methylene chloride=1:9) using silica gel. The solid thus obtained was dissolved in a small amount of methylene chloride, followed by solidification by the addition of diethyl ether, whereby the title compound (50 mg) was obtained as a pale yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionin ethanol (3 ml) was added
  3. stirringthe resulting mixture was stirred at room temperature for 1.5 hours
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. additionwas added with methylene chloride and water
  7. customto separate into layers
  8. extractionThe water layer was extracted with methylene chloride
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customThe residue was purified by preparative thin-layer chromatography (methanol:methylene chloride=1:9)
  13. customThe solid thus obtained

Sources & evidence

ORD record
ord-310f5b8c44154995ad729e529fcc4210
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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