Trifluoroacetic acid → HCID 77745339, compound

HRID 1386640Notes

Reaction equation

HRID 1386640 reaction equation
[CH2:1]([O:8][C:9](=[O:71])[NH:10][CH:11]([C:37](=[O:70])[N:38]([CH:40]([C:56](=[O:69])[NH:57][CH2:58][C:59]1([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH2:62][CH2:61][CH2:60]1)[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:44][CH:43]=1)[CH3:39])[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:71])[NH:10][CH:11]([C:37](=[O:70])[N:38]([CH:40]([C:56](=[O:69])[NH:57][CH2:58][C:59]1([C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH2:62][CH2:61][CH2:60]1)[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[CH:44][CH:43]=1)[CH3:39])[CH2:12][C:13]1[NH:14][CH:15]=[N: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 131722789HCID 131722789, compound

Product 1

HCID 77745339HCID 77745339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [S-[R*,R*)]-[1-({2-(4-Benzyloxy-phenyl)-1-[(1-phenyl-cyclobutymethyl)-carbamoyl}-ethyl}-methyl-carbamoyl)-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester (from Step 3, 1.28 g, 1.36 mmol) in methylene chloride (10 mL) was added TFA (10 mL). The solution was stirred at room temperature for 2 hours and concentrated. The residue was dissolved in ethyl acetate and the solution was washed with saturated NaHCO3, dried over MgSO4, filtered, and concentrated. The residue was purified twice by chromatography (first: CH2Cl2:CH3OH 10:1; second: CH2Cl2:CH3OH 15:1) (0.23 g, 0.33 mmol; 24% yield); MS-APCI 700 (m+1).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified twice by chromatography (first: CH2Cl2:CH3OH 10:1; second: CH2Cl2:CH3OH 15:1) (0.23 g, 0.33 mmol; 24% yield)

Sources & evidence

ORD record
ord-3af7bd428b9f474da593e9c69ddf0a15
Source dataset
uspto-grants-2001_07
Patent number
US06265382B1

Reaction notes

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