Dichloromethane → HCID 66614357, compound

HRID 1615473Notes

Reaction equation

HRID 1615473 reaction equation
Cl[CH:2]1[N:7](C(OC(C)(C)C)=O)[CH2:6][CH:5]([C:15]2[N:23]3[C:18]([C:19]([NH2:24])=[N:20][CH:21]=[N:22]3)=[C:17]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=4)=[C:27]([O:39][CH3:40])[CH:26]=3)[CH:16]=2)[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O.C(OCC)(=O)C.CCCCCC.C(Cl)[Cl:61]>>[Cl:61][C:16]1[C:17]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=3)=[C:27]([O:39][CH3:40])[CH:26]=2)=[C:18]2[N:23]([C:15]=1[CH:5]1[CH2:4][CH2:3][CH2:2][NH:7][CH2:6]1)[N:22]=[CH:21][N:20]=[C:19]2[NH2:24]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 21226206Ethyl acetate hexaneHCID 66611790HCID 66611790, compound

Product 1

HCID 66614357HCID 66614357, compound

Procedure

The compound (40 mg, 0.068 mmol) prepared in Example 30 was taken up in DCM and treated with TFA (0.5 mL). The reaction was stirred for 2 hours and monitored by TLC (1:1 ethyl acetate/hexane). The solvent was removed under vacuum and the residue was taken up in ethyl acetate and the organic layer was washed with 1N sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, brine and dried over anhydrous sodium sulfate. The solution was filtered and solvent removed. The product is used in next reaction without further purification.

Workup

  1. customThe solvent was removed under vacuum
  2. washthe organic layer was washed with 1N sodium hydroxide
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solution was filtered
  7. customsolvent removed
  8. customThe product is used in next reaction without further purification

Sources & evidence

ORD record
ord-5e5b2d49148546db92da1690de212708
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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