Trifluoroacetic acid → HCID 57665527, compound

HRID 2358418Notes

Reaction equation

HRID 2358418 reaction equation
C(O[C:6](=[O:24])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[C:12]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:11][C:10]=1[O:22][CH3:23])(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.C1(OC(=O)[NH:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:51][CH:50]=2)C=CC=CC=1>C(Cl)Cl>[C:55]([C:52]1[CH:51]=[CH:50][C:49]([CH2:48][NH:47][C:6](=[O:24])[NH:7][CH2:8][C:9]2[C:10]([O:22][CH3:23])=[CH:11][C:12]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])=[C:13]([CH:15]=[CH2:16])[CH:14]=2)=[CH:54][CH:53]=1)([CH3:58])([CH3:56])[CH3:57]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 59389711Phenyl [(4-tert-butylphenyl)methyl]carbamateHCID 68453549HCID 68453549, compound

Product 1

HCID 57665527HCID 57665527, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a ice-cooled solution of (4-methanesulfonylamino-2-methoxy-5-vinyl-benzyl)-carbamic acid tert-butyl ester (220 mg, 0.73 mmol) in methylene chloride was treated with trifluoroacetic acid (100 mg, 0.88 mmol)) for 1 hr, and then concentrated under reduced pressure. The part of crude residue (100 mg, 0.27 mmol) was suspended in methylene chloride and treated with triethylamine followed by (4-tert-butyl-benzyl)-carbamic acid phenyl ester (92 mg, 0.32 mmol). The resulting mixture was heated with reflux for 3 days and concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate=1/2) to yield a white solid (8.8 mg, 7.0%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperatureThe resulting mixture was heated
  3. temperaturewith reflux for 3 days
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was column-chromatographed (hexane/ethylacetate=1/2)

Sources & evidence

ORD record
ord-0024d189c3904a8dacea1041f893b313
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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