Dichloromethane → HCID 69894648, compound

HRID 353203Notes

Reaction equation

HRID 353203 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:39])[CH2:15][N:16]([CH2:21][C:22]3[CH:38]=[CH:37][C:25]([O:26][C:27]([CH3:36])([CH3:35])[C:28]([O:30]C(C)(C)C)=[O:29])=[CH:24][CH:23]=3)[CH2:17][CH2:18][O:19][CH3:20])=[C:9]([CH3:40])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[Cl:48]CCl>>[ClH:48].[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:39])[CH2:15][N:16]([CH2:21][C:22]3[CH:38]=[CH:37][C:25]([O:26][C:27]([CH3:36])([CH3:35])[C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)[CH2:17][CH2:18][O:19][CH3:20])=[C:9]([CH3:40])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 18551278HCID 18551278, compound

Product 1

HCID 69894648HCID 69894648, compound

Procedure

0.398 g (0.72 mmol) of the compound from Example 3-10 is initially charged in 5 ml of dichloromethane. At room temperature, 5 ml of trifluoroacetic acid are added. The reaction mixture is stirred at room temperature for 2 hours. The mixture is then concentrated under reduced pressure using a rotary evaporator. The residue is taken up in ethyl acetate and washed with water, 20% strength sodium acetate solution, water and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and freed from the solvent under reduced pressure. The product is purified chromatographically on silica gel (dichloromethane/methanol 30:1). With heating, the residue is dissolved in dichloromethane, 1N hydrochloric acid in diethyl ether is added and n-heptane is added dropwise until the mixture becomes slightly turbid. The product is filtered off with suction, washed with diethyl ether and dried at 40° C. under reduced pressure. This gives 0.187 g (49% of theory) of the title compound.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. customa rotary evaporator
  3. washwashed with water, 20% strength sodium acetate solution, water and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customThe product is purified chromatographically on silica gel (dichloromethane/methanol 30:1)
  6. temperatureWith heating
  7. dissolutionthe residue is dissolved in dichloromethane
  8. addition1N hydrochloric acid in diethyl ether is added
  9. additionn-heptane is added dropwise until the mixture
  10. filtrationThe product is filtered off with suction
  11. washwashed with diethyl ether
  12. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-4b9dd68377af42e1adf4665e8da96072
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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