Trifluoroacetic acid → HCID 86587783, compound

HRID 350383Notes

Reaction equation

HRID 350383 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-3a30b0cc0d2a4376bfe9d38be74c5864
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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