Dichloromethane → HCID 178461491, compound

HRID 846616Notes

Reaction equation

HRID 846616 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[CH3:8][C@@H:9]1[N:12]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)[C:11](=[O:18])[C@H:10]1[NH:19][C:20](=[O:59])/[C:21](/[C:34]1[N:35]=[C:36]([NH:39]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:37][CH:38]=1)=[N:22]\[O:23][C:24](C(C)(C)C)([CH2:26]C(O)=O)[CH3:25].ClCCl>C1(C)C=CC=CC=1>[CH3:8][C@@H:9]1[N:12]([C:13]2[NH:14][N:15]=[N:16][N:17]=2)[C:11](=[O:18])[C@H:10]1[NH:19][C:20](=[O:59])/[C:21](/[C:34]1[N:35]=[C:36]([NH2:39])[S:37][CH:38]=1)=[N:22]\[O:23][C:24]([C:3]([OH:5])=[O:4])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178461492HCID 178461492, compound

Product 1

HCID 178461491HCID 178461491, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (0.50 ml) was added to a -15° solution of 39 (0.047 g, 0.065 mmol) and 0.5 ml dichloromethane. After one hour, the solution was warmed to 23° and stirred for an additional hour before 2 ml toluene was added and volatiles were removed under a stream of nitrogen. Dilution with 10 ml water and washing with 20 ml of 1:1, ethyl acetate: diethyl ether was followed by evaporation under vacuum and chromatography by reverse phase preparative TLC (10% ethanol in water). Elution of a band of Rf 0.9 with 80% acetonitrile in water gave 0.0043 g (16%) 40 as a white solid after lyophilization:

Workup

  1. temperaturethe solution was warmed to 23°
  2. additionwas added
  3. customvolatiles were removed under a stream of nitrogen
  4. washDilution with 10 ml water and washing with 20 ml of 1:1, ethyl acetate
  5. customdiethyl ether was followed by evaporation under vacuum and chromatography by reverse phase preparative TLC (10% ethanol in water)
  6. washElution of a band of Rf 0.9 with 80% acetonitrile in water

Sources & evidence

ORD record
ord-76bc3ddc91fe4b56b92d15853a23121a
Source dataset
uspto-grants-1992_08
Patent number
US05137884

Reaction notes

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