Trifluoroacetic acid → HCID 178521307, compound

HRID 651891Notes

Reaction equation

HRID 651891 reaction equation
[CH2:1]([O:8][C:9](=[O:70])[NH:10][C@H:11]([C:37](=[O:69])[N:38]([CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:57][CH:56]=1)[CH2:39][C:40](=[O:53])[NH:41][CH2:42][C:43]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44]1)[CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:70])[NH:10][C@H:11]([C:37](=[O:69])[N:38]([CH2:54][C:55]1[CH:56]=[CH:57][C:58]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:59][CH:60]=1)[CH2:39][C:40](=[O:53])[NH:41][CH2:42][C:43]1([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:46][CH2:45][CH2:44]1)[CH2:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10748370HCID 10748370, compound

Product 1

HCID 178521307HCID 178521307, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the trityl compound from Step 4 above (0.49 g) in DCM (10 mL) was added TFA (10 mL). The solution was stirred at room temperature for 2 hours and then concentrated. The residue was dissolved in DCM and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM (2×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. Flash chromatography (10% MeOH in DCM) gave 0.22 g (50% yield over two steps) of the title compound as a white foam.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec830883a10a434d8304b4fdf13e728e
Source dataset
uspto-grants-2001_08
Patent number
US06281194B1

Reaction notes

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