Trifluoroacetic acid → 2-Biphenyl-4-ylmethyl-succinic acid 1-methyl ester

HRID 1945054Notes

Reaction equation

HRID 1945054 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7].FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684246972-Biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester

Product 1

HCID 596078292-Biphenyl-4-ylmethyl-succinic acid 1-methyl ester

Procedure

Next, 2-biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester 1-methyl ester (160 mg, 0.451 mmol) is added to trifluoroacetic acid (5 mL). After 10 minutes, the solvent is removed under reduced pressure. Methylene chloride is added and the solvent is removed under reduced pressure to give 2-biphenyl-4-ylmethyl-succinic acid 1-methyl ester. This material is used directly in the subsequent coupling reaction.

Workup

  1. customthe solvent is removed under reduced pressure
  2. additionMethylene chloride is added
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-56e8f233877e4889a0e4380acd1b6704
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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