Trifluoroacetic acid → HCID 117598832, compound

HRID 522401Notes

Reaction equation

HRID 522401 reaction equation
[C:1]([C@H:5]1[C:46](=[O:47])[N:45]2[CH2:48][C@@H:42]([CH2:43][C@H:44]2[C:49](=[O:66])[NH:50][C@:51]2([C:56](=[O:65])[NH:57][S:58]([C:61]3([CH3:64])[CH2:63][CH2:62]3)(=[O:60])=[O:59])[CH2:53][C@H:52]2[CH:54]=[CH2:55])[O:41][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([O:26][CH2:27][C@@H:28]3[O:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:67][C@H:9]2[O:8][C:7](=[O:68])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C@H:5]1[C:46](=[O:47])[N:45]2[CH2:48][C@@H:42]([CH2:43][C@H:44]2[C:49]([NH:50][C@:51]2([C:56](=[O:65])[NH:57][S:58]([C:61]3([CH3:64])[CH2:62][CH2:63]3)(=[O:59])=[O:60])[CH2:53][C@H:52]2[CH:54]=[CH2:55])=[O:66])[O:41][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([O:26][CH2:27][C@@H:28]3[O:33][CH2:32][CH2:31][NH:30][CH2:29]3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:67][C@H:9]2[O:8][C:7](=[O:68])[NH:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117599187HCID 117599187, compound

Product 1

HCID 117598832HCID 117598832, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from step 1 (92 mg) in dichloromethane (0.5 mL) was added trifluoroacetic acid (0.5 mL) The resulting solution was stirred for 3 hours at room temperature until disappearance of the starting material. The solvent was removed in vacuo. The reaction mixture was dissolved in ethyl acetate and a saturated solution of sodium bicarbonate was added slowly. After extracting 3× with ethyl acetate, the combined organics were dried with sodium sulfate, filtered and concentrated to afford the desired product (77.9 mg). LRMS (ES+) m/z 865.45 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe reaction mixture was dissolved in ethyl acetate
  3. additiona saturated solution of sodium bicarbonate was added slowly
  4. extractionAfter extracting 3× with ethyl acetate
  5. dry with materialthe combined organics were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4259282418654f8998b69d936275cfe5
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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