Triethylamine → HCID 20637897, compound

HRID 365800Notes

Reaction equation

HRID 365800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[CH2:11][C@@H:10]3[C:21](=[O:30])[N:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][C:24](=[O:25])[N:9]23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C1COCC1>[CH2:26]([N:22]1[CH2:23][C:24](=[O:25])[N:9]2[C@H:10]([CH2:11][C:12]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[NH:14][C:13]=3[C@@H:8]2[C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:3][CH:4]=2)[C:21]1=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20637915HCID 20637915, compound

Product 1

HCID 20637897HCID 20637897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 98 (0.2 g) in THF (5 mL) was added triethylamine (228 μL) and methanesulfonyl chloride (126 μL) and the solution was heated at reflux for 6 hours. After evaporation of THF, the residue was taken up in CH2Cl2, washed with water and dried over Na2SO4. After evaporation of CH2Cl2, the residue was purified by radial chromatography eluting with CH2Cl2 /MeOH (95/5) to give the title compound as a brown powder (30 mg) m.p.: 188° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 6 hours
  3. customAfter evaporation of THF
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of CH2Cl2
  7. customthe residue was purified by radial chromatography
  8. washeluting with CH2Cl2 /MeOH (95/5)

Sources & evidence

ORD record
ord-62aacf2068a24776b57dc4abfe9c6319
Source dataset
uspto-grants-2000_10
Patent number
US06127542

Reaction notes

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