Trifluoroacetic acid → HCID 89852058, compound

HRID 627146Notes

Reaction equation

HRID 627146 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][CH3:33])[CH:20]=[C:19]1[C:34](=[O:36])[NH2:35])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:34]([NH2:35])=[O:36])=[CH:20][C@@H:21]([CH2:31][O:32][CH3:33])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89863149(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-carbamoyl-2-(methoxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 89852058HCID 89852058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 112 (729 mg, 1.38 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (2133 μl, 27.69 mmol). This solution was slightly darker after addition. The reaction was placed under a nitrogen atmosphere and stirred until LCMS analysis indicated consumption of starting material (˜45 minutes). At that time, solvent was removed in vacuo. The residue was taken up in toluene and sonicated, and then toluene was removed in vacuo. This was repeated twice, affording an orange solid of high purity by proton NMR. The product was taken forward without further purification.

Workup

  1. additionafter addition
  2. customconsumption of starting material (˜45 minutes)
  3. customAt that time, solvent was removed in vacuo
  4. customsonicated
  5. customtoluene was removed in vacuo
  6. customaffording an orange solid of high purity by proton NMR
  7. customThe product was taken forward without further purification

Sources & evidence

ORD record
ord-c91c1c4dcef440028f7e7a76c3efcb6c
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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