Trifluoroacetic acid → Biphenyl-4-carboxylic acid (6-amino-2-hydroxyindan-1-yl)amide

HRID 2053718Notes

Reaction equation

HRID 2053718 reaction equation
C(O[C:6](=[O:19])[NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH2:10][CH:9]1[OH:18])(C)(C)C.C(O)(C(F)(F)F)=O.O=C1CCC(=O)N1OC([C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:39][CH:38]=1)=O>C(Cl)Cl>[NH2:17][C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH:9]([OH:18])[CH:8]2[NH:7][C:6]([C:46]2[CH:47]=[CH:48][C:43]([C:40]3[CH:41]=[CH:42][CH:37]=[CH:38][CH:39]=3)=[CH:44][CH:45]=2)=[O:19])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6847362,5-Dioxopyrrolidin-1-yl [1,1'-biphenyl]-4-carboxylateHCID 22001648(6-Amino-2-hydroxyindan-1-yl)carbamic acid tert-butyl ester

Product 1

HCID 69223853Biphenyl-4-carboxylic acid (6-amino-2-hydroxyindan-1-yl)amideYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (6-amino-2-hydroxyindan-1-yl)carbamic acid tert-butyl ester (1.5 g, 5.68 mmol) with 5 mL of TFA at 0° C. Stir the mixture for 1 h and then evaporate to dryness. Added 3.0 mL of triethylamine and 30 mL of methylene chloride the residue. To this mixture, add a solution of biphenyl-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (1.76 g, 5.96 mmol) in 15 mL of methylene chloride. Stir the resulting mixture for 12 h. Evaporate solvent and purify the residue by a column chromatography (silica gel/MeOH:CH2Cl2=9:1) to give 1.88 g (96% yield) of biphenyl-4-carboxylic acid (6-amino-2-hydroxyindan-1-yl)amide; MS 345 (MH+).

Workup

  1. customat 0° C
  2. customevaporate to dryness
  3. additionAdded 3.0 mL of triethylamine and 30 mL of methylene chloride the residue
  4. stirringStir the resulting mixture for 12 h
  5. customEvaporate solvent and purify the residue by a column chromatography (silica gel/MeOH:CH2Cl2=9:1)

Sources & evidence

ORD record
ord-8f64e39b9f3f42fd82d0e9b95fe43a2e
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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