Trifluoroacetic acid → HCID 67420733, compound

HRID 1037992Notes

Reaction equation

HRID 1037992 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]([CH:20]3[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]4[CH2:32][CH2:31][N:30]([C:33]5[CH:38]=[CH:37][C:36]([C:39]6[N:44]=[CH:43][CH:42]=[CH:41][N:40]=6)=[CH:35][CH:34]=5)[CH2:29][CH2:28]4)[CH2:21]3)=[O:19])=[CH:14][CH:15]=2)[C:10]([NH:46][C:47](=[O:49])[CH3:48])=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:47]([NH:46][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([NH:17][C:18]([CH:20]3[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:45])[N:27]4[CH2:28][CH2:29][N:30]([C:33]5[CH:38]=[CH:37][C:36]([C:39]6[N:44]=[CH:43][CH:42]=[CH:41][N:40]=6)=[CH:35][CH:34]=5)[CH2:31][CH2:32]4)[CH2:21]3)=[O:19])[CH:12]=2)[NH:8][N:9]=1)(=[O:49])[CH3:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67420818HCID 67420818, compound

Product 1

HCID 67420733HCID 67420733, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 37 from Step 2 (20 mg, 0.03 mmol) 37 in CH2Cl2 (2 mL) was added TFA (2 mL) at rt. The crude was stirred at rt for 17 hrs. The crude was quenched with sat. NaHCO3 at rt. The crude was partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, dried over MgSO4, filtered, and evaporated. The crude was chromatographed to give 6.1 mg of the product.

Workup

  1. customThe crude was quenched with sat. NaHCO3 at rt
  2. customThe crude was partitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was chromatographed

Sources & evidence

ORD record
ord-d0627eb6b193410da6d1ae04614b8d52
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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