Trifluoroacetic acid → HCID 77745339, compound

HRID 1582742Notes

Reaction equation

HRID 1582742 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, compoundYield 24%

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-c4685845e1f841829976b18ca9fd6571
Source dataset
uspto-grants-2004_05
Patent number
US06737410B1

Reaction notes

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