Trifluoroacetic acid → HCID 86587783, compound

HRID 354321Notes

Reaction equation

HRID 354321 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12](C(OC(C)(C)C)=O)[C@H:11]([CH2:21][O:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[N+:33]([O-:35])=[O:34])[CH2:10]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@H:9]1[CH2:13][NH:12][C@H:11]([CH2:21][O:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[N+:33]([O-:35])=[O:34])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587784HCID 86587784, compound

Product 1

HCID 86587783HCID 86587783, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl (2S, 4R)-4-[4-benzyloxy-1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-nitrobenzoate (681 mg, 1.4 mmol) in CH2Cl2 (2 mL) was added TFA (2 mL), and the resulting mixture was stirred for 2 hr. After the reaction mixture was concentrated, the residue was made basic by the addition of sat. NaHCO3 and extracted with CHCl3. The extract was washed with H2O, dried over MgSO4, and evaporated to give 511 mg (95%) methyl (2S, 4R)-4-[4-benzyloxy-2-pyrrolidinyl]methoxy-3-nitrobenzoate as a yellow oil.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionthe residue was made basic by the addition of sat. NaHCO3
  3. extractionextracted with CHCl3
  4. washThe extract was washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-bb2dcb0d3c56484fb5c5a6b6184a9ab6
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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